Heterocyclic compound and organic light emitting element comprising same

ABSTRACT

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.

TECHNICAL FIELD

The present specification relates to a heterocyclic compound and anorganic light emitting device comprising the same.

BACKGROUND ART

An electroluminescent device is one type of self-emissive displaydevices, and has an advantage of having a wide viewing angle, and a highresponse speed as well as having an excellent contrast.

An organic light emitting device has a structure disposing an organicthin film between two electrodes. When a voltage is applied to anorganic light emitting device having such a structure, electrons andholes injected from the two electrodes bind and pair in the organic thinfilm, and light emits as these annihilate. The organic thin film may beformed in a single layer or a multilayer as necessary.

A material of the organic thin film may have a light emitting functionas necessary. For example, as a material of the organic thin film,compounds capable of forming a light emitting layer themselves alone maybe used, or compounds capable of performing a role of a host or a dopantof a host-dopant-based light emitting layer may also be used. Inaddition thereto, compounds capable of performing roles of holeinjection, hole transfer, electron blocking, hole blocking, electrontransfer, electron injection and the like may also be used as a materialof the organic thin film.

Development of an organic thin film material has been continuouslyrequired for enhancing performance, lifetime or efficiency of an organiclight emitting device.

DISCLOSURE Technical Problem

The present disclosure is directed to providing a heterocyclic compoundand an organic light emitting device comprising the same.

Technical Solution

One embodiment of the present application provides a heterocycliccompound represented by the following Chemical Formula 1.

In Chemical Formula 1,

X is O or S,

L1 and L2 are the same as or different from each other, and eachindependently a substituted or unsubstituted arylene group; or asubstituted or unsubstituted heteroarylene group,

Z1 and Z2 are the same as or different from each other, and eachindependently hydrogen; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted aryl group; a substituted or unsubstitutedheteroaryl group; —SiRR′R″; or —P(═O)RR′,

R_(a) and R_(b) are the same as or different from each other, and eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted alkynyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted heterocycloalkyl group; a substituted or unsubstitutedaryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

R, R′ and R″ are the same as or different from each other, and eachindependently hydrogen; deuterium; —CN; a substituted or unsubstitutedalkyl group; a substituted or unsubstituted cycloalkyl group; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group,

p and n are an integer of 1 to 3,

m, q and s are an integer of 1 to 4,

r is an integer of 0 to 4, and

when r is an integer of 0 and Z2 is hydrogen, n is an integer of 2 or 3,and R_(b) is a substituted or unsubstituted aryl group; or a substitutedor unsubstituted heteroaryl group, or two or more groups adjacent toeach other bond to each other to form a substituted or unsubstitutedaliphatic or aromatic hydrocarbon ring.

Another embodiment of the present application provides an organic lightemitting device comprising a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layerscomprise the heterocyclic compound represented by Chemical Formula 1.

Advantageous Effects

The compound described in the present specification can be used as anorganic material layer material of an organic light emitting device. Thecompound is capable of performing a role of a hole injection material, ahole transfer material, a light emitting material, an electron transfermaterial, an electron injection material and the like in the organiclight emitting device. Particularly, the heterocyclic compoundrepresented by Chemical Formula 1 can be used as an electron transferlayer material, a hole blocking layer material or a charge generationlayer material of the organic light emitting device. In addition, whenusing the compound represented by Chemical Formula 1 in the organicmaterial layer, a driving voltage is lowered and light efficiency isenhanced in the device, and device lifetime properties can be enhancedby thermal stability of the compound.

Particularly, the heterocyclic compound represented by Chemical Formula1 has both N-type and P-type substituents in one core structure, and byhaving a P-type substituent, hole properties can be strengthened in themolecule. The compound of Chemical Formula 1 is a bipolar type havingboth a P-type and an N-type, and is thereby capable of blocking holeleakage and effectively trapping excitons in a light emitting layer. Inaddition, hole properties are strengthened in a specific devicestructure changing electron mobility relatively slowly, which balanceselectrons and holes in the light emitting layer properly forming arecombination region of the excitons, and as a result, efficiency andlifetime increase.

DESCRIPTION OF DRAWINGS

FIG. 1 to FIG. 4 are diagrams each schematically illustrating alamination structure of an organic light emitting device according toone embodiment of the present application.

REFERENCE NUMERAL

-   -   100: Substrate    -   200: Anode    -   300: Organic Material Layer    -   301: Hole Injection Layer    -   302: Hole Transfer Layer    -   303: Light Emitting Layer    -   304: Hole Blocking Layer    -   305: Electron Transfer Layer    -   306: Electron Injection Layer    -   400: Cathode

MODE FOR DISCLOSURE

Hereinafter, the present application will be described in detail.

The term “substituted” means a hydrogen atom bonding to a carbon atom ofa compound is changed to another substituent, and the position ofsubstitution is not limited as long as it is a position at which thehydrogen atom is substituted, that is, a position at which a substituentcan substitute, and when two or more substituents substitute, the two ormore substituents may be the same as or different from each other.

In the present specification, the halogen may be fluorine, chlorine,bromine or iodine.

In the present specification, the alkyl group comprises linear orbranched having 1 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkyl groupmay be from 1 to 60, specifically from 1 to 40 and more specificallyfrom 1 to 20. Specific examples thereof may comprise a methyl group, anethyl group, a propyl group, an n-propyl group, an isopropyl group, abutyl group, an n-butyl group, an isobutyl group, a tert-butyl group, asec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, atert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentylgroup, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, ann-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, acyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octylgroup, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentylgroup, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propylgroup, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentylgroup, a 4-methylhexyl group, a 5-methylhexyl group and the like, butare not limited thereto.

In the present specification, the alkenyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkenyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20. Specific examples thereof may comprise a vinyl group, a1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, anallyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-ylgroup, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, astyrenyl group and the like, but are not limited thereto.

In the present specification, the alkynyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkynyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20.

In the present specification, the alkoxy group may be linear, branchedor cyclic. The number of carbon atoms of the alkoxy group is notparticularly limited, but is preferably from 1 to 20. Specific examplesthereof may comprise methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy,isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy,isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy,n-octyloxy, n-nonyloxy, n-decyloxy, benxyloxy, p-methylbenzyloxy and thelike, but are not limited thereto.

In the present specification, the cycloalkyl group comprises monocyclicor multicyclic having 3 to 60 carbon atoms, and may be furthersubstituted with other substituents. Herein, the multicyclic means agroup in which the cycloalkyl group is directly linked to or fused withother cyclic groups. Herein, the other cyclic groups may be a cycloalkylgroup, but may also be different types of cyclic groups such as aheterocycloalkyl group, an aryl group and a heteroaryl group. The numberof carbon groups of the cycloalkyl group may be from 3 to 60,specifically from 3 to 40 and more specifically from 5 to 20. Specificexamples thereof may comprise a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a 3-methylcyclopentyl group, a2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexylgroup, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, acycloheptyl group, a cyclooctyl group and the like, but are not limitedthereto.

In the present specification, the heterocycloalkyl group comprises O, S,Se, N or Si as a heteroatom, comprises monocyclic or multicyclic having2 to 60 carbon atoms, and may be further substituted with othersubstituents. Herein, the multicyclic means a group in which theheterocycloalkyl group is directly linked to or fused with other cyclicgroups. Herein, the other cyclic groups may be a heterocycloalkyl group,but may also be different types of cyclic groups such as a cycloalkylgroup, an aryl group and a heteroaryl group. The number of carbon atomsof the heterocycloalkyl group may be from 2 to 60, specifically from 2to 40 and more specifically from 3 to 20.

In the present specification, the aryl group comprises monocyclic ormulticyclic having 6 to 60 carbon atoms, and may be further substitutedwith other substituents. Herein, the multicyclic means a group in whichthe aryl group is directly linked to or fused with other cyclic groups.Herein, the other cyclic groups may be an aryl group, but may also bedifferent types of cyclic groups such as a cycloalkyl group, aheterocycloalkyl group and a heteroaryl group. The aryl group comprisesa spiro group. The number of carbon atoms of the aryl group may be from6 to 60, specifically from 6 to 40 and more specifically from 6 to 25.Specific examples of the aryl group may comprise a phenyl group, abiphenyl group, a triphenyl group, a naphthyl group, an anthryl group, achrysenyl group, a phenanthrenyl group, a perylenyl group, afluoranthenyl group, a triphenylenyl group, a phenalenyl group, apyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenylgroup, an indenyl group, an acenaphthylenyl group, a benzofluorenylgroup, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a fusedring thereof, and the like, but are not limited thereto.

In the present specification, the silyl group is a substituentcomprising Si, having the Si atom directly linked as a radical, and isrepresented by —SiR₁₀₄R₁₀₅R₁₀₆. R₁₀₄ to R₁₀₆ are the same as ordifferent from each other, and may be each independently a substituentformed with at least one of hydrogen; deuterium; a halogen group; analkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; anaryl group; and a heterocyclic group. Specific examples of the silylgroup may comprise a trimethylsilyl group, a triethylsilyl group, at-butyldimethylsilyl group, a vinyldimethylsilyl group, apropyldimethylsilyl group, a triphenylsilyl group, a diphenylsilylgroup, a phenylsilyl group and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted,and adjacent substituents may bond to each other to form a ring.

When the fluorenyl group is substituted,

and the like may be included. However, the structure is not limitedthereto.

In the present specification, the heteroaryl group comprises O, S, Se, Nor Si as a heteroatom, comprises monocyclic or multicyclic having 2 to60 carbon atoms, and may be further substituted with other substituents.Herein, the multicyclic means a group in which the heteroaryl group isdirectly linked to or fused with other cyclic groups. Herein, the othercyclic groups may be a heteroaryl group, but may also be different typesof cyclic groups such as a cycloalkyl group, a heterocycloalkyl groupand an aryl group. The number of carbon atoms of the heteroaryl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom to 25. Specific examples of the heteroaryl group may comprise apyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group,a furanyl group, a thiophene group, an imidazolyl group, a pyrazolylgroup, an oxazolyl group, an isoxazolyl group, a triazolyl group, anisothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolylgroup, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, apyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group,a triazinyl group, a dioxynyl group, a triazinyl group, a tetrazinylgroup, a quinolyl group, an isoquinolyl group, a quinazolinyl group, anisoquinazolinyl group, a qninozolinyl group, a naphthyridyl group, anacridinyl group, a phenanthridinyl group, an imidazopyridinyl group, adiazanaphthalenyl group, a triazaindene group, an indolyl group, anindolizinyl group, a benzothiazolyl group, a benzoxazolyl group, abenzimidazolyl group, a benzothiophene group, a benzofuran group, adibenzothiophene group, a dibenzofuran group, a carbazolyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, a phenazinyl group, adibenzosilole group, spirobi(dibenzosilole), a dihydrophenazinyl group,a phenoxazinyl group, a phenanthridyl group, an imidazopyridinyl group,a thienyl group, an indolo[2,3-a]carbazolyl group, anindolo[2,3-b]carbazolyl group, an indolinyl group, a10,11-dihydro-dibenzo[b,f]azepine group, a 9,10-dihydroacridinyl group,a phenanthrazinyl group, a phenothiathiazinyl group, a phthalazinylgroup, a naphthylidinyl group, a phenanthrolinyl group, abenzo[c][1,2,5]thiadiazolyl group, a5,10-dihydrobenzo[b,e][1,4]azasilinyl, a pyrazolo[1,5-c]quinazolinylgroup, a pyrido[1,2-b]indazolyl group, apyrido[1,2-a]imidazo[1,2-e]indolinyl group, a5,11-dihydroindeno[1,2-b]carbazolyl group and the like, but are notlimited thereto.

In the present specification, the amine group may be selected from thegroup consisting of a monoalkylamine group; a monoarylamine group; amonoheteroarylamine group; —NH₂; a dialkylamine group; a diarylaminegroup; a diheteroarylamine group; an alkylarylamine group; analkylheteroarylamine group; and an arylheteroarylamine group, andalthough not particularly limited thereto, the number of carbon atoms ispreferably from 1 to 30. Specific examples of the amine group maycomprise a methylamine group, a dimethylamine group, an ethylaminegroup, a diethylamine group, a phenylamine group, a naphthylamine group,a biphenylamine group, a dibiphenylamine group, an anthracenylaminegroup, a 9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, a biphenylnaphthylamine group, aphenylbiphenylamine group, a biphenylfluorenylamine group, aphenyltriphenylenylamine group, a biphenyltriphenylenylamine group andthe like, but are not limited thereto.

In the present specification, the arylene group means the aryl grouphaving two bonding sites, that is, a divalent group. Descriptions on thearyl group provided above may be applied thereto except for each being adivalent. In addition, the heteroarylene group means the heteroarylgroup having two bonding sites, that is, a divalent group. Descriptionson the heteroaryl group provided above may be applied thereto except foreach being a divalent.

In the present specification, specific examples of the phosphine oxidegroup may comprise a diphenylphosphine oxide group, adinaphthylphosphine oxide group and the like, but are not limitedthereto.

In the present specification, an “adjacent” group may mean a substituentsubstituting an atom directly linked to an atom substituted by thecorresponding substituent, a substituent sterically most closelypositioned to the corresponding substituent, or another substituentsubstituting an atom substituted by the corresponding substituent. Forexample, two substituents substituting ortho positions in a benzenering, and two substituents substituting the same carbon in an aliphaticring may be interpreted as groups “adjacent” to each other.

In the present specification, the term “substituted” means a hydrogenatom bonding to a carbon atom of a compound is changed to anothersubstituent, and the position of substitution is not limited as long asit is a position at which the hydrogen atom is substituted, that is, aposition at which a substituent can substitute, and when two or moresubstituents substitute, the two or more substituents may be the same asor different from each other.

In the present specification, “substituted or unsubstituted” means beingsubstituted with one or more substituents selected from the groupconsisting of C1 to C60 linear or branched alkyl; C2 to C60 linear orbranched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclicheterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60monocyclic or polycyclic heteroaryl; —SiRR′R″; P(═O)RR′; C1 to C20alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60monocyclic or polycyclic heteroarylamine, or being unsubstituted, orbeing substituted with a substituent linking two or more substituentsselected from among the substituents illustrated above, or beingunsubstituted.

One embodiment of the present application provides a compoundrepresented by Chemical Formula 1.

In one embodiment of the present application, X of Chemical Formula 1may be 0 or S.

In one embodiment of the present application, X of Chemical Formula 1may be O.

In one embodiment of the present application, X of Chemical Formula 1may be S.

In one embodiment of the present application, R_(a) of Chemical Formula1 may be selected from the group consisting of hydrogen; deuterium; ahalogen group; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted alkynyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted heterocycloalkyl group; a substituted or unsubstitutedaryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other may bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, R_(a) of Chemical Formula 1 may be hydrogen; asubstituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group.

In another embodiment, R_(a) of Chemical Formula 1 may be hydrogen; asubstituted or unsubstituted C6 to C60 aryl group; or a substituted orunsubstituted C2 to C60 heteroaryl group.

In another embodiment, R_(a) of Chemical Formula 1 may be hydrogen; a C6to C30 aryl group; or a C2 to C30 heteroaryl group.

In another embodiment, R_(a) of Chemical Formula 1 may be hydrogen.

In one embodiment of the present application, L1 may be a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group.

In another embodiment, L1 may be a substituted or unsubstituted C6 toC60 arylene group; or a substituted or unsubstituted C2 to C60heteroarylene group.

In another embodiment, L1 may be a substituted or unsubstituted C6 toC40 arylene group; or a substituted or unsubstituted C2 to C40heteroarylene group.

In another embodiment, L1 may be a substituted or unsubstitutedmonocyclic or polycyclic C6 to C40 arylene group; or a substituted orunsubstituted C2 to C40 N-containing heteroarylene group.

In another embodiment, L1 may be a monocyclic or polycyclic C6 to C40arylene group; or a C2 to C40 N-containing heteroarylene group.

In another embodiment, L1 may be a phenylene group; a biphenylene group;a triphenylenylene group; a naphthylene group; a phenanthrenylene group;a divalent pyridine group; a divalent pyrimidine group; a divalentphenanthroline group or a divalent triazine group.

In one embodiment of the present application, Z1 may be hydrogen; asubstituted or unsubstituted alkyl group; a substituted or unsubstitutedaryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″;or —P(═O)RR′.

In another embodiment, Z1 may be hydrogen; a substituted orunsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroarylgroup; —SiRR′R″; or —P(═O)RR′.

In another embodiment, Z1 may be hydrogen; a substituted orunsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroarylgroup; —SiRR′R″; or —P(═O)RR′.

In another embodiment, Z1 may be hydrogen; a substituted orunsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 toC40 heteroaryl group; or —P(═O)RR′.

In another embodiment, Z1 may be hydrogen; a C6 to C40 aryl groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of a C6 to C40 aryl group and a C2 to C40heteroaryl group; a C2 to C40 heteroaryl group; or —P(═O)RR′.

In another embodiment, Z1 may be hydrogen; a phenyl group unsubstitutedor substituted with a carbazole group, a dibenzofuran group or adibenzothiophene group; a biphenyl group; a dibenzofuran group; adibenzothiophene group; a pyridine group; a pyrimidine group; a triazinegroup; or —P(═O)RR′.

In one embodiment of the present application, R_(b) of Chemical Formula1 may be selected from the group consisting of hydrogen; deuterium; ahalogen group; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted alkenyl group; a substituted orunsubstituted alkynyl group; a substituted or unsubstituted alkoxygroup; a substituted or unsubstituted cycloalkyl group; a substituted orunsubstituted heterocycloalkyl group; a substituted or unsubstitutedaryl group; a substituted or unsubstituted heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other may bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, R_(b) of Chemical Formula 1 may be selected fromthe group consisting of hydrogen; a substituted or unsubstituted C1 toC60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; asubstituted or unsubstituted C2 to C60 heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedaryl group, or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other may bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, R_(b) of Chemical Formula 1 may be selected fromthe group consisting of hydrogen; a substituted or unsubstituted C6 toC60 aryl group; and a substituted or unsubstituted C2 to C60 heteroarylgroup, or two or more groups adjacent to each other may bond to eachother to form a substituted or unsubstituted aliphatic or aromatichydrocarbon ring.

In another embodiment, R_(b) of Chemical Formula 1 may be selected fromthe group consisting of hydrogen; a substituted or unsubstituted C6 toC40 aryl group; and a substituted or unsubstituted C2 to C40 heteroarylgroup, or two or more groups adjacent to each other may bond to eachother to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another embodiment, R_(b) of Chemical Formula 1 may be selected fromthe group consisting of hydrogen; a C6 to C40 aryl group unsubstitutedor substituted with one or more substituents selected from the groupconsisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group;and a C2 to C40 heteroaryl group, or two or more groups adjacent to eachother may bond to each other to form C6 to C40 aromatic hydrocarbonring.

In another embodiment, R_(b) of Chemical Formula 1 may be selected fromthe group consisting of hydrogen; a phenyl group unsubstituted orsubstituted with one or more substituents selected from the groupconsisting of a triphenylene group, a phenanthrene group, adibenzothiophene group and a dibenzofuran group; a biphenyl group; anaphthyl group; a phenanthrene group; a triphenylene group; adibenzofuran group; and a dibenzothiophene group, or two or more groupsadjacent to each other may bond to each other to form a benzene ring.

In one embodiment of the present application, L2 may be a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group.

In another embodiment, L2 may be a substituted or unsubstituted C6 toC60 arylene group; or a substituted or unsubstituted C2 to C60heteroarylene group.

In another embodiment, L2 may be a substituted or unsubstituted C6 toC40 arylene group; or a substituted or unsubstituted C2 to C40heteroarylene group.

In another embodiment, L2 may be a C6 to C40 arylene group; or a C2 toC40 heteroarylene group.

In another embodiment, L2 may be a phenylene group; a biphenylene group;a triphenylenylene group; a phenanthrenylene group; a divalent pyridinegroup; a divalent pyrimidine group; a divalent quinoline group; adivalent phenanthroline group or a divalent triazine group.

In one embodiment of the present application, Z2 may be hydrogen; asubstituted or unsubstituted aryl group; a substituted or unsubstitutedheteroaryl group; or P(═O)RR′.

In another embodiment, Z2 may be hydrogen; a substituted orunsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 toC60 heteroaryl group; or P(═O)RR′.

In another embodiment, Z2 may be hydrogen; a substituted orunsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 toC40 heteroaryl group; or P(═O)RR′.

In another embodiment, Z2 may be hydrogen; a C6 to C40 aryl groupunsubstituted or substituted with a C6 to C40 heteroaryl group; a C2 toC40 heteroaryl group; or P(═O)RR′.

In another embodiment, Z2 may be hydrogen; a phenyl group unsubstitutedor substituted with a carbazole group, a dibenzofuran group or adibenzothiophene group; a biphenyl group; a pyridine group; a pyrimidinegroup; a triazine group; or P(═O)RR′.

In one embodiment of the present application, R, R′ and R″ are the sameas or different from each other, and may be each independently hydrogen;deuterium; —CN; a substituted or unsubstituted alkyl group; asubstituted or unsubstituted cycloalkyl group; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently hydrogen; a substituted orunsubstituted aryl group; or a substituted or unsubstituted heteroarylgroup.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently hydrogen; a substituted orunsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2to C60 heteroaryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a substituted or unsubstitutedC6 to C60 aryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a C6 to C60 aryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a C6 to C40 aryl group.

In another embodiment, R, R′ and R″ are the same as or different fromeach other, and may be each independently a phenyl group.

In one embodiment of the present application, p of Chemical Formula 1may be 1.

In one embodiment of the present application, p of Chemical Formula 1may be 2.

In one embodiment of the present application, p of Chemical Formula 1may be 3.

In one embodiment of the present application, q of Chemical Formula 1may be 1.

In one embodiment of the present application, q of Chemical Formula 1may be 2.

In one embodiment of the present application, q of Chemical Formula 1may be 3.

In one embodiment of the present application, r of Chemical Formula 1may be 0.

In one embodiment of the present application, r of Chemical Formula 1may be 1.

In one embodiment of the present application, r of Chemical Formula 1may be 2.

In one embodiment of the present application, r of Chemical Formula 1may be 3.

In one embodiment of the present application, s of Chemical Formula 1may be 1.

In one embodiment of the present application, s of Chemical Formula 1may be 2.

In one embodiment of the present application, s of Chemical Formula 1may be 3.

In one embodiment of the present application, s of Chemical Formula 1may be 4.

In one embodiment of the present application, when r is an integer of 0and Z2 is hydrogen in Chemical Formula 1, n is an integer of 2 or 3, andR_(b) is a substituted or unsubstituted aryl group; or a substituted orunsubstituted heteroaryl group, or two or more groups adjacent to eachother bond to each other to form a substituted or unsubstitutedaliphatic or aromatic hydrocarbon ring.

In another embodiment, when r is an integer of 0 and Z2 is hydrogen inChemical Formula 1, n is an integer of 2, and adjacent two R_(b)s maybond to each other to form a substituted or unsubstituted aliphatic oraromatic hydrocarbon ring.

In another embodiment, when r is an integer of 0 and Z2 is hydrogen inChemical Formula 1, n is an integer of 2, and adjacent two R_(b)s maybond to each other to form a substituted or unsubstituted aromatichydrocarbon ring.

In another embodiment, when r is an integer of 0 and Z2 is hydrogen inChemical Formula 1, n is an integer of 2, and adjacent two R_(b)s maybond to each other to form a substituted or unsubstituted C3 to C60aromatic hydrocarbon ring.

In another embodiment, when r is an integer of 0 and Z2 is hydrogen inChemical Formula 1, n is an integer of 2, and adjacent two R_(b)s maybond to each other to form a substituted or unsubstituted C3 to C30aromatic hydrocarbon ring.

In another embodiment, when r is an integer of 0 and Z2 is hydrogen inChemical Formula 1, n is an integer of 2, and adjacent two R_(b)s maybond to each other to form a C3 to C30 aromatic hydrocarbon ring.

In another embodiment, when r is an integer of 0 and Z2 is hydrogen inChemical Formula 1, n is an integer of 2, and adjacent two R_(b)s maybond to each other to form a benzene ring.

In the heterocyclic compound provided in one embodiment of the presentapplication, Chemical Formula 1 is represented by any one of thefollowing Chemical Formulae 2 to 5.

In Chemical Formulae 2 to 5,

L1, L2, Z1, Z2, X, p, q, r and s each have the same definition as inChemical Formula 1.

In the heterocyclic compound provided in one embodiment of the presentapplication, Chemical Formula 1 is represented by any one of thefollowing Chemical Formulae 6 to 11.

In Chemical Formulae 6 to 11,

R_(a), L1, Z1, p, q and m each have the same definition as in ChemicalFormula 1.

The heterocyclic compound represented by Chemical Formula 1 has bothN-type and P-type substituents in one core structure, and by having aP-type substituent, hole properties may be strengthened in the molecule.The compound of Chemical Formula 1 is a bipolar type having both aP-type and an N-type, and is thereby capable of blocking hole leakageand effectively trapping excitons in a light emitting layer. Inaddition, hole properties are strengthened in a specific devicestructure changing electron mobility relatively slowly, which balanceselectrons and holes in the light emitting layer properly forming arecombination region of the excitons, and as a result, efficiency andlifetime increase.

In the heterocyclic compound provided in one embodiment of the presentapplication, Chemical Formula 1 is represented by any one of thefollowing compounds.

The compound according to one embodiment of the present application maybe prepared according to the following General Formula 1.

In General Formula 1, X has the same definition as X in Chemical Formula1, and R10 or R11 has the same definition as

of Chemical Formula 1.

In addition, by introducing various substituents to the structures ofChemical Formulae 1 to 11, compounds having unique properties of theintroduced substituents may be synthesized. For example, by introducingsubstituents normally used as hole injection layer materials, holetransfer layer materials, light emitting layer materials, electrontransfer layer materials and charge generation layer materials used formanufacturing an organic light emitting device to the core structure,materials satisfying conditions required for each organic material layermay be synthesized.

In addition, by introducing various substituents to the structures ofChemical Formulae 1 to 11, the energy band gap may be finely controlled,and meanwhile, properties at interfaces between organic materials areenhanced, and material applications may become diverse.

Meanwhile, the compound has a high glass transition temperature (Tg),and has excellent thermal stability. Such an increase in the thermalstability becomes an important factor providing driving stability to adevice.

Another embodiment of the present application provides an organic lightemitting device comprising a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layerscomprise the heterocyclic compound.

In one embodiment of the present application, the first electrode may bean anode, and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode, and thesecond electrode may be an anode.

In one embodiment of the present application, the organic light emittingdevice may be a blue organic light emitting device, and the heterocycliccompound according to Chemical Formula 1 may be used as a material ofthe blue organic light emitting device.

In one embodiment of the present application, the organic light emittingdevice may be a green organic light emitting device, and theheterocyclic compound according to Chemical Formula 1 may be used as amaterial of the green organic light emitting device.

In one embodiment of the present application, the organic light emittingdevice may be a red organic light emitting device, and the heterocycliccompound according to Chemical Formula 1 may be used as a material ofthe red organic light emitting device.

Specific descriptions on the heterocyclic compound represented byChemical Formula 1 are the same as the descriptions provided above.

The organic light emitting device of the present disclosure may bemanufactured using common organic light emitting device manufacturingmethods and materials except that one or more organic material layersare formed using the heterocyclic compound described above.

The heterocyclic compound may be formed into an organic material layerthrough a solution coating method as well as a vacuum deposition methodwhen manufacturing the organic light emitting device. Herein, thesolution coating method means spin coating, dip coating, inkjetprinting, screen printing, a spray method, roll coating and the like,but is not limited thereto.

The organic material layer of the organic light emitting device of thepresent disclosure may be formed in a single layer structure, or mayalso be formed in a multilayer structure in which two or more organicmaterial layers are laminated. For example, the organic light emittingdevice according to one embodiment of the present disclosure may have astructure comprising a hole injection layer, a hole transfer layer, alight emitting layer, an electron transfer layer, an electron injectionlayer and the like as the organic material layer. However, the structureof the organic light emitting device is not limited thereto, and maycomprise less numbers of organic material layers.

In the organic light emitting device of the present disclosure, theorganic material layer may comprise a light emitting layer, and thelight emitting layer may comprise the heterocyclic compound representedby Chemical Formula 1.

In another organic light emitting device, the organic material layercomprises a light emitting layer, the light emitting layer comprises ahost material, and the host material may comprise the heterocycliccompound represented by Chemical Formula 1.

In another embodiment, the organic material layer comprising theheterocyclic compound comprises the heterocyclic compound represented byChemical Formula 1 as a host, and may be used together with aphosphorescent dopant.

In another embodiment, the organic material layer comprising theheterocyclic compound comprises the heterocyclic compound represented byChemical Formula 1 as a host, and may be used together with aniridium-based dopant.

As a material of the phosphorescent dopant, those known in the art maybe used.

For example, phosphorescent dopant materials represented by LL′MX,LL′L″M, LMXX′, L2MX and L3M may be used, however, the scope of thepresent disclosure is not limited to these examples.

Herein, L, L′, L″, X and X′ are bidentate ligands different from eachother, and M is a metal forming an octahedral complex.

M may comprise iridium, platinum, osmium or the like.

L is an anionic bidentate ligand coordinated to M as the iridium-baseddopant by sp2 carbon and heteroatom, and X may perform a function oftrapping electrons or holes. Nonlimiting examples of L may comprise2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole),(2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8-benzoquinoline),(thiophene group pyrizine), phenylpyridine, benzothiophene grouppyrizine, 3-methoxy-2-phenylpyridine, thiophene group pyrizine,tolylpyridine and the like. Nonlimiting examples of X may compriseacetylacetonate (acac), hexafluoroacetylacetonate, salicylidene,picolinate, 8-hydroxyquinolate and the like.

More specific examples thereof are presented below, however, thephosphorescent dopant is not limited to these examples.

In one embodiment of the present application, as the iridium-baseddopant, Ir(ppy)₃ may be used as a green phosphorescent dopant.

In one embodiment of the present application, the dopant content may befrom 1% to 15%, preferably from 3% to 10% and more preferably from 5% to10% based on the whole light emitting layer.

In the organic light emitting device of the present disclosure, theorganic material layer comprises an electron injection layer or anelectron transfer layer, and the electron injection layer or theelectron transfer layer may comprise the heterocyclic compound.

In another organic light emitting device, the organic material layercomprises an electron blocking layer or a hole blocking layer, and theelectron blocking layer or the hole blocking layer may comprise theheterocyclic compound.

In another organic light emitting device, the organic material layercomprises an electron transfer layer, a light emitting layer or a holeblocking layer, and the electron transfer layer, the light emittinglayer or the hole blocking layer may comprise the heterocyclic compound.

The organic light emitting device of the present disclosure may furthercomprise one, two or more layers selected from the group consisting of alight emitting layer, a hole injection layer, a hole transfer layer, anelectron injection layer, an electron transfer layer, an electronblocking layer and a hole blocking layer.

FIGS. 1 to 3 illustrate a lamination order of electrodes and organicmaterial layers of an organic light emitting device according to oneembodiment of the present application. However, the scope of the presentapplication is not limited to these diagrams, and structures of organiclight emitting devices known in the art may also be used in the presentapplication.

FIG. 1 illustrates an organic light emitting device in which an anode(200), an organic material layer (300) and a cathode (400) areconsecutively laminated on a substrate (100). However, the structure isnot limited to such a structure, and as illustrated in FIG. 2, anorganic light emitting device in which a cathode, an organic materiallayer and an anode are consecutively laminated on a substrate may alsobe obtained.

FIG. 3 illustrates a case of the organic material layer being amultilayer. The organic light emitting device according to FIG. 3comprises a hole injection layer (301), a hole transfer layer (302), alight emitting layer (303), a hole blocking layer (304), an electrontransfer layer (305) and an electron injection layer (306). However, thescope of the present application is not limited to such a laminationstructure, and as necessary, other layers except the light emittinglayer may not be included, and other necessary functional layers may befurther included.

The organic material layer comprising Chemical Formula 1 may furthercomprise other materials as necessary.

In addition, the organic light emitting device according to oneembodiment of the present application comprises a first electrode, asecond electrode, and two or more stacks provided between the firstelectrode and the second electrode, wherein the two or more stacks eachindependently comprise a light emitting layer, a charge generation layeris included between the two or more stacks, and the charge generationlayer comprises the heterocyclic compound represented by ChemicalFormula 1.

In addition, the organic light emitting device according to oneembodiment of the present application may comprise a first electrode, afirst stack provided on the first electrode and comprising a first lightemitting layer, a charge generation layer provided on the first stack, asecond stack provided on the charge generation layer and comprising asecond light emitting layer, and a second electrode provided on thesecond stack. Herein, the charge generation layer may comprise theheterocyclic compound represented by Chemical Formula 1. In addition,the first stack and the second stack may each independently furthercomprise one or more types of the hole injection layer, the holetransfer layer, the hole blocking layer, the electron transfer layer,the electron injection layer described above and the like.

The charge generation layer may be an N-type charge generation layer,and the charge generation layer may further comprise a dopant known inthe art in addition to the heterocyclic compound represented by ChemicalFormula 1.

As the organic light emitting device according to one embodiment of thepresent application, an organic light emitting device having a 2-stacktandem structure is schematically illustrated in FIG. 4.

The organic material layer comprising Chemical Formula 1 may furthercomprise other materials as necessary.

In the organic light emitting device according to one embodiment of thepresent application, materials other than the compound of ChemicalFormula 1 are illustrated below, however, these are for illustrativepurposes only and not for limiting the scope of the present application,and may be replaced by materials known in the art.

As the anode material, materials having relatively large work functionmay be used, and transparent conductive oxides, metals, conductivepolymers or the like may be used. Specific examples of the anodematerial comprise metals such as vanadium, chromium, copper, zinc andgold, or alloys thereof; metal oxides such as zinc oxide, indium oxide,indium tin oxide (ITO) and indium zinc oxide (IZO); combinations ofmetals and oxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole and polyaniline, and the like, but are not limitedthereto.

As the cathode material, materials having relatively small work functionmay be used, and metals, metal oxides, conductive polymers or the likemay be used. Specific examples of the cathode material comprise metalssuch as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

As the hole injection material, known hole injection materials may beused, and for example, phthalocyanine compounds such as copperphthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-typeamine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA),4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB)described in the literature [Advanced Material, 6, p. 677 (1994)],polyaniline/dodecylbenzene sulfonic acid,poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate),polyaniline/camphor sulfonic acid orpolyaniline/poly(4-styrene-sulfonate) that are conductive polymershaving solubility, and the like, may be used.

As the hole transfer material, pyrazoline derivatives, arylamine-basedderivatives, stilbene derivatives, triphenyldiamine derivatives and thelike may be used, and low molecular or high molecular materials may alsobe used.

As the electron transfer material, metal complexes of oxadiazolederivatives, anthraquinodimethane and derivatives thereof, benzoquinoneand derivatives thereof, naphthoquinone and derivatives thereof,anthraquinone and derivatives thereof, tetracyanoanthraquinodimethaneand derivatives thereof, fluorenone derivatives, diphenyldicyanoethyleneand derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinolineand derivatives thereof, and the like, may be used, and high molecularmaterials may also be used as well as low molecular materials.

As examples of the electron injection material, LiF is typically used inthe art, however, the present application is not limited thereto.

As the light emitting material, red, green or blue light emittingmaterials may be used, and as necessary, two or more light emittingmaterials may be mixed and used. Herein, two or more light emittingmaterials may be used by being deposited as individual sources of supplyor by being premixed and deposited as one source of supply. In addition,fluorescent materials may also be used as the light emitting material,however, phosphorescent materials may also be used. As the lightemitting material, materials emitting light by bonding electrons andholes injected from an anode and a cathode, respectively, may be usedalone, however, materials having a host material and a dopant materialinvolved in light emission together may also be used.

When mixing light emitting material hosts, same series hosts may bemixed, or different series hosts may be mixed. For example, any two ormore types of materials among n-type host materials or P-type hostmaterials may be selected, and used as a host material of a lightemitting layer.

The organic light emitting device according to one embodiment of thepresent application may be a top-emission type, a bottom-emission typeor a dual-emission type depending on the materials used.

The heterocyclic compound according to one embodiment of the presentapplication may also be used in an organic electronic device comprisingan organic solar cell, an organic photo conductor, an organic transistorand the like under a similar principle used in the organic lightemitting device.

Hereinafter, the present specification will be described in more detailwith reference to examples, however, these are for illustrative purposesonly, and the scope of the present application is not limited thereto.

PREPARATION EXAMPLE <Preparation Example 1>—Preparation of Compound 1

1) Preparation of Compound 1-5

After dissolving benzo[b]thiophen-3-ylboronic acid (162 g, 1000 mmol)and 2-bromo-6-chloroaniline (189 g, 1100 mmol) in toluene, EtOH and H₂O(2000 mL:400 mL:400 mL), Pd(PPh₃)₄ (58 g, 50 mmol) and NaHCO₃ (252 g,3000 mmol) were introduced thereto, and the result was refluxed for 4hours. After the reaction was completed, the result was cooled to roomtemperature and extracted with MC. The result was dried with anhydrousMgSO4, and then the solvent was removed using a rotary evaporator.Target Compound 1-5 was obtained using column chromatography(MC:Hx=1:3). (190 g, 91%, brown oil)

2) Preparation of Compound 1-4

Compound 1-5 (95 g, 428 mmol) and triethylamine (190 mL, 1362 mmol) wereintroduced to MC (1500 mL) and dissolved therein. 4-Bromobenzoylchloride (149 g, 681 mmol) dissolved in MC (300 mL) was slowly addeddropwise to the mixture at 0° C. After the reaction was completed, MCand distilled water were introduced to the reaction solution forextraction. After that, the result was dried with anhydrous MgSO4, and,after removing the solvent using a rotary evaporator, recrystallizedwith EA/Hx to obtain Compound 1-4. (82 g, 91%, white solid)

3) Preparation of Compound 1-3

After dissolving Compound 1-4 (82 g, 210 mmol) in nitrobenzene (1000mL), POCl₃ (24 mL, 210 mmol) was slowly added dropwise thereto. Afterthat, the result was stirred for 12 hours at 150° C. After the reactionwas completed, the reaction solution was neutralized with an aqueousNaHCO₃ solution. Solids produced from the neutralization were filtered.The solids were recrystallized with MC/MeOH to obtain target Compound1-3. (69 g, 88%, white solid)

4) Preparation of Compound 1-2

After dissolving Compound 1-3 (61 g, 163 mmol), bis(pinacolato)diboron(62 g, 244 mmol), Pd(dppf)Cl₂ (6 g, 8.2 mmol) and KOAc (48 g, 489 mmol)in 1,4-dioxane (600 mL), the result was refluxed for 12 hours. After thereaction was completed, MC and distilled water were introduced to thereaction solution for extraction. After that, the result was dried withanhydrous MgSO4, and the solvent was removed using a rotary evaporator.After passing silica, the result went through MeOH slurry to obtainCompound 1-2. (69 g, 95%, pale pink solid)

5) Preparation of Compound 1-1

After dissolving Compound 1-2 (9cw g, 21.4 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (8.2 g, 21.4 mmol) in toluene, EtOHand H₂O (100 mL:20 mL:20 mL), Pd(PPh₃)₄ (1.3 g, 1.07 mmol) and K₂CO₃(8.9 g, 64.2 mol) were introduced thereto, and the result was refluxedfor 5 hours. After the reaction was completed, produced solids werefiltered to obtain Compound 1-1. (11.4 g, 88%, white solid)

5) Preparation of Compound 1

After dissolving Compound 1-1 (10 g, 17.3 mmol), triphenylen-2-ylboronicacid (5.7 g, 20.8 mmol), Pd₂(dba)₃ (1.6 g, 1.7 mmol), XPhos (1.7 g, 3.4mmol) and K₃PO₄ (11 g, 52 mmol) in 1,4-dioxane (100 mL), the result wasrefluxed for 12 hours. After the reaction was finished, produced solidswere filtered. The solids were washed with distilled water and acetoneto obtain target Compound 1. (9 g, 65%, white solid)

A target compound was synthesized in the same manner as in PreparationExample 1 except that Intermediate A of the following Table 1 was usedinstead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate B ofthe following Table 1 was used instead of triphenylen-2-ylboronic acid.

TABLE 1 Com- pound Num- ber Intermediate A Intermediate B TargetCompound Yield 7

70% 10

69% 14

75% 72

61% 75

66% 78

70% 125

75% 130

62% 179

70% 182

66% 921

68%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 3-bromobenzoyl chloride was used instead of4-bromobenzoyl chloride, Intermediate C of the following Table 2 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate Dof the following Table 2 was used instead of triphenylen-2-ylboronicacid.

TABLE 2 Com- pound Num- ber Intermediate C Intermediate D TargetCompound Yield 134

70% 197

69% 925

70%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, Intermediate E of the following Table 3 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate Fof the following Table 3 was used instead of triphenylen-2-ylboronicacid.

TABLE 3 Com- pound Num- ber Intermediate E Intermediate F TargetCompound Yield 17

71% 28

69% 83

75% 89

68% 138

60% 143

65% 149

70% 186

68% 199

64%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, 3-bromobenzoyl chloride was used instead of4-bromobenzoyl chloride, Intermediate G of the following Table 4 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate Hof the following Table 4 was used instead of triphenylen-2-ylboronicacid.

TABLE 4 Com- pound Num- ber Intermediate G Intermediate H TargetCompound Yield  25

66%  31

69%  91

75% 926

61%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, Intermediate I of the following Table 5 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate Jof the following Table 5 was used instead of triphenylen-2-ylboronicacid.

TABLE 5 Com- pound Num- ber Intermediate I Intermediate J TargetCompound Yield  33

71%  51

62%  56

75%  57

68%  98

64% 100

71% 103

55% 106

62% 151

64% 156

70% 159

66% 190

59% 203

60%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, Intermediate K of the following Table 6 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate Lof the following Table 6 was used instead of triphenylen-2-ylboronicacid.

TABLE 6 Compound Number Intermediate K Intermediate L Target CompoundYield  59

71%  68

62% 112

75% 117

63% 119

67% 166

71% 207

70%

A target compound was synthesized in the same manner as in PreparationExample 1 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, 3-bromobenzoyl chloride was used instead of4-bromobenzoyl chloride, Intermediate M of the following Table 7 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate Nof the following Table 7 was used instead of triphenylen-2-ylboronicacid.

TABLE 7 Compound Number Intermediate M Intermediate N Target CompoundYield  69

71% 171

62% 174

75% 178

67%

<Preparation Example 2>—Preparation of Compound 212

1) Preparation of Compound 212-4

After dissolving benzo[b]thiophen-3-ylboronic acid (80 g, 500 mmol) and2-bromo-6-chloroaniline (95 g, 550 mmol) in toluene, EtOH and H₂O (1500mL:300 mL:300 mL), Pd(PPh₃)₄ (29 g, 25 mmol) and NaHCO₃ (126 g, 1500mmol) were introduced thereto, and the result was refluxed for 4 hours.After the reaction was completed, the result was cooled to roomtemperature and extracted with MC. The result was dried with anhydrousMgSO4, and then the solvent was removed using a rotary evaporator.Target Compound 212-4 was obtained using column chromatography(MC:Hx=1:3). (90 g, 91%, brown oil)

2) Preparation of Compound 212-3

Compound 212-4 (90 g, 219 mmol) and triethylamine (95 mL, 660 mmol) wereintroduced to MC (1500 mL) and dissolved therein. Benzoyl chloride (80g, 250 mmol) dissolved in MC (300 mL) was slowly added dropwise to themixture at 0° C. After the reaction was completed, MC and distilledwater were introduced to the reaction solution for extraction. Afterthat, the result was dried with anhydrous MgSO4, and, after removing thesolvent using a rotary evaporator, recrystallized with EA/Hx to obtainCompound 212-3. (100 g, 91%, white solid)

3) Preparation of Compound 212-2

After dissolving Compound 212-3 (40 g, 110 mmol) in nitrobenzene (400mL), POCl₃ (13 mL, 110 mmol) was slowly added dropwise thereto. Afterthat, the result was stirred for 12 hours at 150° C. After the reactionwas completed, the reaction solution was neutralized with an aqueousNaHCO₃ solution. Solids produced from the neutralization were filtered.The solids were recrystallized with MC/MeOH to obtain target Compound212-2. (30 g, 88%, white solid)

4) Preparation of Compound 212-1

After dissolving Compound 212-2 (30 g, 70 mmol), bis(pinacolato)diboron(27 g, 105 mmol), Pd(dba)₂ (4 g, 7 mmol), XPhos (6.8 g, 14 mmol) andKOAc (48 g, 210 mmol) in 1,4-dioxane (300 mL), the result was refluxedfor 12 hours. After the reaction was completed, MC and distilled waterwere introduced to the reaction solution for extraction. After that, theresult was dried with anhydrous MgSO4, and the solvent was removed usinga rotary evaporator. After passing silica, the result went through MeOHslurry to obtain Compound 212-1. (34 g, 85%, white solid)

5) Preparation of Compound 212

After dissolving Compound 212-1 (10 g, 22.9 mmol),9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole(13 g, 22.9 mmol), Pd(PPh₃)₄ (1.3 g, 1.2 mmol) and K₂CO₃ (10 g, 69 mmol)in toluene, EtOH and H₂O (100 mL:20 mL:20 mL), the result was refluxedfor 12 hours. After the reaction was finished, produced solids werefiltered. The solids were washed with distilled water and acetone toobtain target Compound 212. (9 g, 65%, white solid)

A target compound was synthesized in the same manner as in PreparationExample 2 except that Intermediate 0 of the following Table 8 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 8 Compound Number Intermediate O Target Compound Yield 228

60% 243

70% 259

69% 272

58% 929

60%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 1-naphthoyl chloride was used instead of benzoylchloride, and Intermediate P of the following Table 9 was used insteadof9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 9 Compound Number Intermediate P Target Compound Yield 283

71%

A target compound was synthesized in the same manner as in PreparationExample 2 except that phenanthrene-9-carbonyl chloride was used insteadof benzoyl chloride, and Intermediate Q of the following Table 10 wasused instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 10 Compound Number Intermediate Q Target Compound Yield 379

66%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, and Intermediate R of the following Table 11was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 11 Compound Number Intermediate R Target Compound Yield 217

67% 231

70% 233

61% 263

65%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, 1-naphthoyl chloride was used instead ofbenzoyl chloride, and Intermediate S of the following Table 12 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 12 Com- pound Number Intermediate S Target Compound Yield 288

61% 305

70% 319

58% 334

63% 347

66%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate T of the following Table13 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 13 Com- pound Num- ber Intermediate T Target Compound Yield 358

65% 373

72% 382

58% 389

61%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, triphenylene-2-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate U of the following Table14 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 14 Compound Number Intermediate U Target Compound Yield 397

73%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, and Intermediate V of the following Table 15was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 15 Com- pound Num- ber Intermediate V Target Compound Yield 219

77% 236

73% 252

55% 253

60% 265

71% 278

68%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, 1-naphthoyl chloride was used instead ofbenzoyl chloride, and Intermediate W of the following Table 16 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 16 Com- pound Num- ber Intermediate W Target Compound Yield 293

77% 308

73% 324

71%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate X of the following Table17 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 17 Compound Number Intermediate X Target Compound Yield 367

67%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, triphenylene-2-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate Y of the following Table18 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 18 Compound Number Intermediate Y Target Compound Yield 415

67% 419

75%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, and Intermediate Z of the following Table 19was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 19 Compound Number Intermediate Z Target Compound Yield 223

54% 256

53%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, 1-naphthoyl chloride was used instead ofbenzoyl chloride, and Intermediate AA of the following Table 20 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 20 Compound Number Intermediate AA Target Compound Yield 295

56% 328

53% 352

59%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate AB of the following Table21 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 21 Compound Number Intermediate AB Target Compound Yield 393

51%

A target compound was synthesized in the same manner as in PreparationExample 2 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate AC of the following Table22 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 22 Compound Number Intermediate AC Target Compound Yield 406

53%

<Preparation Example 3>—Preparation of Compound 425

1) Preparation of Compound 425-4

After dissolving benzo[b]thiophen-3-ylboronic acid (40 g, 250 mmol) and2-bromonaphthalen-1-amine (67 g, 300 mmol) in toluene, EtOH and H₂O(1000 mL:200 mL:200 mL), Pd(PPh₃)₄ (15 g, 13 mmol) and NaHCO₃ (63 g, 750mmol) were introduced thereto, and the result was refluxed for 4 hours.After the reaction was completed, the result was cooled to roomtemperature and extracted with MC. The result was dried with anhydrousMgSO4, and then the solvent was removed using a rotary evaporator.Target Compound 425-4 was obtained using column chromatography(MC:Hx=1:3). (60 g, 88%, brown solid)

2) Preparation of Compound 425-3

Compound 425-4 (60 g, 218 mmol) and triethylamine (93 mL, 650 mmol) wereintroduced to MC (1500 mL) and dissolved therein. 4-Bromobenzoylchloride (53 g, 240 mmol) dissolved in MC (300 mL) was slowly addeddropwise to the mixture at 0° C. After the reaction was completed, MCand distilled water were introduced to the reaction solution forextraction. After that, the result was dried with anhydrous MgSO4, and,after removing the solvent using a rotary evaporator, recrystallizedwith EA/Hx to obtain Compound 425-3. (90 g, 90%, white solid)

3) Preparation of Compound 425-2

After dissolving Compound 425-3 (90 g, 200 mmol) in nitrobenzene (400mL), POCl₃ (24 mL, 200 mmol) was slowly added dropwise thereto. Afterthat, the result was stirred for 12 hours at 150° C. After the reactionwas completed, the reaction solution was neutralized with an aqueousNaHCO₃ solution. Solids produced from the neutralization were filtered.The solids were recrystallized with MC/MeOH to obtain target Compound425-2. (70 g, 80%, white solid)

4) Preparation of Compound 425-1

After dissolving Compound 425-2 (70 g, 159 mmol), bis(pinacolato)diboron(50 g, 191 mmol), Pd(dppf)Cl₂ (5.8 g, 8 mmol) and KOAc (48 g, 477 mmol)in 1,4-dioxane (300 mL), the result was refluxed for 12 hours. After thereaction was completed, MC and distilled water were introduced to thereaction solution for extraction. After that, the result was dried withanhydrous MgSO4, and the solvent was removed using a rotary evaporator.After passing silica, the result went through MeOH slurry to obtainCompound 425-1. (66 g, 85%, white solid)

5) Preparation of Compound 425

After dissolving Compound 425-1 (10 g, 20.5 mmol),4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7 g, 20.5 mmol),Pd(PPh₃)₄ (1.2 g, 1.1 mmol) and K₂CO₃ (8.5 g, 62 mmol) in toluene, EtOHand H₂O (100 mL:20 mL:20 mL), the result was refluxed for 12 hours.After the reaction was finished, produced solids were filtered. Thesolids were washed with distilled water and acetone to obtain targetCompound 425. (11 g, 82%, white solid)

A target compound was synthesized in the same manner as in PreparationExample 3 except that Intermediate AD of the following Table 23 was usedinstead of 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine

TABLE 23 Compound Number Intermediate AD Target Compound Yield 423

85% 433

90% 937

91%

A target compound was synthesized in the same manner as in PreparationExample 3 except that 3-bromonaphthalen-2-amine was used instead of2-bromonaphthalen-1-amine, and Intermediate AE of the following Table 24was used instead of 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine

TABLE 24 Com- pound Num- ber Intermediate AE Target Compound Yield 435

85% 441

90% 444

88% 938

82%

A target compound was synthesized in the same manner as in PreparationExample 3 except that 1-bromonaphthalen-2-amine was used instead of2-bromonaphthalen-1-amine, and Intermediate AF of the following Table 25was used instead of4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine.

TABLE 25 Compound Number Intermediate AF Target Compound Yield 453

82% 455

86% 460

85% 942

86%

<Preparation Example 4>—Preparation of Compound 461

1) Preparation of Compound 461-5

After dissolving benzofuran-3-ylboronic acid (162 g, 1000 mmol) and2-bromo-6-chloroaniline (189 g, 1100 mmol) in toluene, EtOH and H₂O(2000 mL:400 mL:400 mL), Pd(PPh₃)₄ (58 g, 50 mmol) and NaHCO₃ (252 g,3000 mmol) were introduced thereto, and the result was refluxed for 4hours. After the reaction was completed, the result was cooled to roomtemperature and extracted with MC. The result was dried with anhydrousMgSO4, and then the solvent was removed using a rotary evaporator.Target Compound 461-5 was obtained using column chromatography(MC:Hx=1:3). (190 g, 91%, brown oil)

2) Preparation of Compound 461-4

Compound 461-5 (95 g, 428 mmol) and triethylamine (190 mL, 1362 mmol)were introduced to MC (1500 mL) and dissolved therein. 4-Bromobenzoylchloride (149 g, 681 mmol) dissolved in MC (300 mL) was slowly addeddropwise to the mixture at 0° C. After the reaction was completed, MCand distilled water were introduced to the reaction solution forextraction. After that, the result was dried with anhydrous MgSO4, and,after removing the solvent using a rotary evaporator, recrystallizedwith MC/Hx to obtain Compound 461-4. (82 g, 91%, white solid)

3) Preparation of Compound 461-3

After dissolving Compound 461-4 (82 g, 210 mmol) in nitrobenzene (1000mL), POCl₃ (24 mL, 210 mmol) was slowly added dropwise thereto. Afterthat, the result was stirred for 12 hours at 150° C. After the reactionwas completed, the reaction solution was neutralized with an aqueousNaHCO₃ solution. Solids produced from the neutralization were filtered.The solids were recrystallized with MC/MeOH to obtain target Compound461-3. (69 g, 88%, white solid)

4) Preparation of Compound 461-2

After dissolving Compound 461-2 (61 g, 163 mmol), bis(pinacolato)diboron(62 g, 244 mmol), Pd(dppf)Cl₂ (6 g, 8.2 mmol) and KOAc (48 g, 489 mmol)in 1,4-dioxane (600 mL), the result was refluxed for 12 hours. After thereaction was completed, MC and distilled water were introduced to thereaction solution for extraction. After that, the result was dried withanhydrous MgSO4, and the solvent was removed using a rotary evaporator.After passing silica, the result went through MeOH slurry to obtainCompound 461-2. (69 g, 95%, pale pink solid)

5) Preparation of Compound 461-1

After dissolving Compound 461-2 (9cw g, 21.4 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (8.2 g, 21.4 mmol) in toluene, EtOHand H₂O (100 mL:20 mL:20 mL), Pd(PPh₃)₄ (1.3 g, 1.07 mmol) and K₂CO₃(8.9 g, 64.2 mol) were introduced thereto, and the result was refluxedfor 5 hours. After the reaction was completed, produced solids werefiltered to obtain Compound 461-1. (10 g, 78%, white solid)

5) Preparation of Compound 461

After dissolving Compound 461-1 (10 g, 17.3 mmol),triphenylen-2-ylboronic acid (5.7 g, 20.8 mmol), Pd₂(dba)₃ (1.6 g, 1.7mmol), XPhos (1.7 g, 3.4 mmol) and K₃PO₄ (11 g, 52 mmol) in 1,4-dioxane(100 mL), the result was refluxed for 12 hours. After the reaction wasfinished, produced solids were filtered. The solids were washed withdistilled water and acetone to obtain target Compound 461. (9 g, 65%,white solid)

A target compound was synthesized in the same manner as in PreparationExample 4 except that Intermediate AG of the following Table 26 was usedinstead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate AH ofthe following Table 26 was used instead of triphenylen-2-ylboronic acid.

TABLE 26 Compound Intermediate Intermediate Number AG AH 467

470

474

532

535

538

585

590

639

642

Compound Number Target Compound Yield 467

69% 470

70% 474

72% 532

64% 535

66% 538

71% 585

71% 590

67% 639

65% 642

69%

A target compound was synthesized in the same manner as in PreparationExample 4 except that 3-bromobenzoyl chloride was used instead of4-bromobenzoyl chloride, Intermediate AI of the following Table 27 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and IntermediateAJ of the following Table 27 was used instead of triphenylen-2-ylboronicacid.

TABLE 27 Compound Intermediate Intermediate Number AI AJ Target CompoundYield 594

71% 657

61%

A target compound was synthesized in the same manner as in PreparationExample 4 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, Intermediate AK of the following Table 28 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and IntermediateAL of the following Table 28 was used instead of triphenylen-2-ylboronicacid.

TABLE 28 Compound Intermediate Intermediate Number AK AL 477

488

543

549

598

603

609

646

659

Compound Number Target Compound Yield 477

58% 488

72% 543

68% 549

71% 598

68% 603

61% 609

58% 646

68% 659

67%

A target compound was synthesized in the same manner as in PreparationExample 4 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, 3-bromobenzoyl chloride was used instead of4-bromobenzoyl chloride, Intermediate AM of the following Table 29 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and IntermediateAN of the following Table 29 was used instead of triphenylen-2-ylboronicacid.

TABLE 29 Compound Intermediate Intermediate Number AM AN 485

491

551

Compound Number Target Compound Yield 485

69% 491

61% 551

72%

A target compound was synthesized in the same manner as in PreparationExample 4 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, Intermediate AO of the following Table 30 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and IntermediateAP of the following Table 30 was used instead of triphenylen-2-ylboronicacid.

TABLE 30 Compound Intermediate Intermediate Number AO AP 493

511

516

517

558

560

563

566

611

616

619

650

663

Compound Number Target Compound Yield 493

63% 511

66% 516

70% 517

62% 558

67% 560

73% 563

59% 566

69% 611

64% 616

58% 619

61% 650

54% 663

65%

A target compound was synthesized in the same manner as in PreparationExample 4 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, Intermediate AQ of the following Table 31 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and IntermediateAR of the following Table 31 was used instead of triphenylen-2-ylboronicacid.

TABLE 31 Compound Number Intermediate AQ Intermediate AR Target CompoundYield 519

66% 528

67% 572

70% 577

66% 579

61% 626

70% 667

59% 924

62%

A target compound was synthesized in the same manner as in PreparationExample 4 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, 3-bromobenzoyl chloride was used instead of4-bromobenzoyl chloride, Intermediate AS of the following Table 32 wasused instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and IntermediateAT of the following Table 32 was used instead of triphenylen-2-ylboronicacid.

TABLE 32 Compound Number Intermediate AS Intermediate AT Target CompoundYield 529

65% 631

65% 634

63% 638

65% 928

61%

<Preparation Example 5>—Preparation of Compound 672

1) Preparation of Compound 672-4

After dissolving benzofuran-3-ylboronic acid (80 g, 500 mmol) and2-bromo-6-chloroaniline (95 g, 550 mmol) in toluene, EtOH and H₂O (1500mL:300 mL:300 mL), Pd(PPh₃)₄ (29 g, 25 mmol) and NaHCO₃ (126 g, 1500mmol) were introduced thereto, and the result was refluxed for 4 hours.After the reaction was completed, the result was cooled to roomtemperature and extracted with MC. The result was dried with anhydrousMgSO4, and then the solvent was removed using a rotary evaporator.Target Compound 672-4 was obtained using column chromatography(MC:Hx=1:3). (80 g, 80%, brown oil)

2) Preparation of Compound 672-3

Compound 672-4 (90 g, 219 mmol) and triethylamine (95 mL, 660 mmol) wereintroduced to MC (1500 mL) and dissolved therein. Benzoyl chloride (80g, 250 mmol) dissolved in MC (300 mL) was slowly added dropwise to themixture at 0° C. After the reaction was completed, MC and distilledwater were introduced to the reaction solution for extraction. Afterthat, the result was dried with anhydrous MgSO4, and, after removing thesolvent using a rotary evaporator, recrystallized with MC/Hx to obtainCompound 672-3. (100 g, 91%, white solid)

3) Preparation of Compound 672-2

After dissolving Compound 672-3 (40 g, 110 mmol) in nitrobenzene (400mL), POCl₃ (13 mL, 110 mmol) was slowly added dropwise thereto. Afterthat, the result was stirred for 12 hours at 150° C. After the reactionwas completed, the reaction solution was neutralized with an aqueousNaHCO₃ solution. Solids produced from the neutralization were filtered.The solids were recrystallized with MC/MeOH to obtain target Compound672-2. (30 g, 88%, white solid)

4) Preparation of Compound 672-1

After dissolving Compound 672-2 (30 g, 70 mmol), bis(pinacolato)diboron(27 g, 105 mmol), Pd(dba)₂ (4 g, 7 mmol), XPhos (6.8 g, 14 mmol) andKOAc (48 g, 210 mmol) in 1,4-dioxane (300 mL), the result was refluxedfor 12 hours. After the reaction was completed, MC and distilled waterwere introduced to the reaction solution for extraction. After that, theresult was dried with anhydrous MgSO4, and the solvent was removed usinga rotary evaporator. After passing silica, the result went through MeOHslurry to obtain Compound 672-2. (34 g, 85%, white solid)

5) Preparation of Compound 672

After dissolving Compound 672-1 (10 g, 22.9 mmol),9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole(13 g, 22.9 mmol), Pd(PPh₃)₄ (1.3 g, 1.2 mmol) and K₂CO₃ (10 g, 69 mmol)in toluene, EtOH and H₂O (100 mL:20 mL:20 mL), the result was refluxedfor 12 hours. After the reaction was finished, produced solids werefiltered. The solids were washed with distilled water and acetone toobtain target Compound 672. (10 g, 70%, white solid)

A target compound was synthesized in the same manner as in PreparationExample 5 except that Intermediate AU of the following Table 33 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 33 Compound Number Intermediate AU Target Compound Yield 688

65% 703

71% 719

67% 732

58%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 1-naphthoyl chloride was used instead of benzoylchloride, and Intermediate AV of the following Table 34 was used insteadof9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 34 Compound Number Intermediate AV Target Compound Yield 743

95%

A target compound was synthesized in the same manner as in PreparationExample 5 except that phenanthrene-9-carbonyl chloride was used insteadof benzoyl chloride, and Intermediate AW of the following Table 35 wasused instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 35 Compound Number Intermediate AW Target Compound Yield 839

66%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, and Intermediate AX of the following Table 36was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 36 Compound Number Intermediate AX Target Compound Yield 677

67% 691

71% 693

67% 723

65%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, 1-naphthoyl chloride was used instead ofbenzoyl chloride, and Intermediate AY of the following Table 37 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 37 Compound Number Intermediate AY Target Compound Yield 748

61% 765

78% 779

58% 794

69% 807

66%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate AZ of the following Table38 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 38 Compound Number Intermediate AZ Target Compound Yield 818

60% 833

72% 842

60% 849

61%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-5-chloroaniline was used instead of2-bromo-6-chloroaniline, triphenylene-2-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate BA of the following Table39 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 39 Compound Number Intermediate BA Target Compound Yield 857

68%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, and Intermediate BB of the following Table 40was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 40 Compound Number Intermediate BB Target Compound Yield 679

71% 696

67% 712

60% 713

60% 725

71% 738

68%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, 1-naphthoyl chloride was used instead ofbenzoyl chloride, and Intermediate BC of the following Table 41 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 41 Compound Number Intermediate BC Target Compound Yield 753

77% 768

73% 784

71% 935

80%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate BD of the following Table42 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 42 Compound Number Intermediate BD Target Compound Yield 827

67% 931

65%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-4-chloroaniline was used instead of2-bromo-6-chloroaniline, triphenylene-2-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate BE of the following Table43 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 43 Compound Number Intermediate BE Target Compound Yield 875

64% 879

63%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, and Intermediate BF of the following Table 44was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 44 Compound Number Intermediate BF Target Compound Yield 683

60% 716

56%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, 1-naphthoyl chloride was used instead ofbenzoyl chloride, and Intermediate BG of the following Table 45 was usedinstead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 45 Compound Number Intermediate BG Target Compound Yield 755

56% 788

52% 812

59%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate BH of the following Table46 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 46 Compound Number Intermediate BH Target Compound Yield 853

51%

A target compound was synthesized in the same manner as in PreparationExample 5 except that 2-bromo-3-chloroaniline was used instead of2-bromo-6-chloroaniline, phenanthrene-9-carbonyl chloride was usedinstead of benzoyl chloride, and Intermediate BI of the following Table47 was used instead of9-(4-(4-(4-bromophenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole.

TABLE 47 Compound Number Intermediate BI Target Compound Yield 866

53%

<Preparation Example 6>—Preparation of Compound 885

1) Preparation of Compound 885-4

After dissolving benzofuran-3-ylboronic acid (40 g, 250 mmol) and2-bromonaphthalen-1-amine (67 g, 300 mmol) in toluene, EtOH and H₂O(1000 mL:200 mL:200 mL), Pd(PPh₂)₄ (15 g, 13 mmol) and NaHCO₃ (63 g, 750mmol) were introduced thereto, and the result was refluxed for 4 hours.After the reaction was completed, the result was cooled to roomtemperature and extracted with MC. The result was dried with anhydrousMgSO4, and then the solvent was removed using a rotary evaporator.Target Compound 885-4 was obtained using column chromatography(MC:Hx=1:3). (50 g, 78%, brown solid)

2) Preparation of Compound 885-3

Compound 885-4 (60 g, 218 mmol) and triethylamine (93 mL, 650 mmol) wereintroduced to MC (1500 mL) and dissolved therein. 4-Bromobenzoylchloride (53 g, 240 mmol) dissolved in MC (300 mL) was slowly addeddropwise to the mixture at 0° C. After the reaction was completed, MCand distilled water were introduced to the reaction solution forextraction. After that, the result was dried with anhydrous MgSO4, and,after removing the solvent using a rotary evaporator, recrystallizedwith EA/Hx to obtain Compound 885-3. (90 g, 90%, white solid)

3) Preparation of Compound 885-2

After dissolving Compound 885-3 (90 g, 200 mmol) in nitrobenzene (400mL), POCl₃ (24 mL, 200 mmol) was slowly added dropwise thereto. Afterthat, the result was stirred for 12 hours at 150° C. After the reactionwas completed, the reaction solution was neutralized with an aqueousNaHCO₃ solution. Solids produced from the neutralization were filtered.The solids were recrystallized with MC/MeOH to obtain target Compound885-2. (60 g, 70%, white solid)

4) Preparation of Compound 885-1

After dissolving Compound 885-2 (70 g, 159 mmol), bis(pinacolato)diboron(50 g, 191 mmol), Pd(dppf)Cl₂ (5.8 g, 8 mmol) and KOAc (48 g, 477 mmol)in 1,4-dioxane (300 mL), the result was refluxed for 12 hours. After thereaction was completed, MC and distilled water were introduced to thereaction solution for extraction. After that, the result was dried withanhydrous MgSO4, and the solvent was removed using a rotary evaporator.After passing silica, the result went through MeOH slurry to obtainCompound 885-1. (66 g, 85%, white solid)

5) Preparation of Compound 885

After dissolving Compound 885-1 (10 g, 20.5 mmol),4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7 g, 20.5 mmol),Pd(PPh₃)₄ (1.2 g, 1.1 mmol) and K₂CO₃ (8.5 g, 62 mmol) in toluene, EtOHand H₂O (100 mL:20 mL:20 mL), the result was refluxed for 12 hours.After the reaction was finished, produced solids were filtered. Thesolids were washed with distilled water and acetone to obtain targetCompound 885. (9 g, 72%, white solid)

A target compound was synthesized in the same manner as in PreparationExample 6 except that Intermediate BJ of the following Table 48 was usedinstead of 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine.

TABLE 48 Compound Number Intermediate BJ Target Compound Yield 883

75% 893

80% 940

81%

A target compound was synthesized in the same manner as in PreparationExample 6 except that 3-bromonaphthalen-2-amine was used instead of2-bromonaphthalen-1-amine, and Intermediate BK of the following Table 49was used instead of4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine.

TABLE 49 Compound Number Intermediate BK Target Compound Yield 895

75% 901

80% 904

78% 944

82%

A target compound was synthesized in the same manner as in PreparationExample 6 except that 1-bromonaphthalen-2-amine was used instead of2-bromonaphthalen-1-amine, and Intermediate BL of the following Table 50was used instead of4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine.

TABLE 50 Compound Number Intermediate BL Target Compound Yield 913

72% 915

76% 920

75% 939

3%

The following Table 51 and Table 52 present 1H NMR data and FD-MS dataof the synthesized compounds, and through the following data, synthesesof target compounds are identified.

TABLE 51 Compound Number ¹H NMR (CDCl₃, 400 Mhz) 1 δ = 9.15(s, 1H),8.93(d, 2H), 8.81(d, 2H), 8.45(d, 1H), 8.28-7.98(m, 11H), 8.05(d, 2H),7.88-7.82(m, 6H), 7.66(t, 1H), 7.52-7.41(m, 8H) 7 δ = 8.81(d, 2H),8.55(d, 1H), 8.45(d, 1H), 8.28(d, 2H), 8.21(d, 1H), 8.12(d, 1H),8.02-7.94(m, 3H), 7.88(d, 2H), 7.79(d, 2H), 7.68-7.63(m, 4H),7.52-7.41(m, 9H), 7.33-7.19(m, 5H) 10 δ = 8.81(d, 2H), 8.45(d, 1H),8.28(dd, 2H), 8.21(d, 1H), 8.02-7.98(m, 2H), 7.89-7.81(m, 7H), 7.66(td,2H), 7.52-7.50(m, 6H), 7.41-7.19(m, 9H) 14 δ = 8.81(d, 2H), 8.45(d, 1H),8.28(dd, 4H), 8.21(d, 1H), 8.00(d, 2H), 7.89-7.85(m, 7H), 7.66(td, 2H),7.52- 7.50(m, 6H), 7.41-7.25(m, 7H) 17 δ = 9.15(s, 1H), 8.93(d, 2H),8.81(d, 2H), 8.45(d, 1H), 8.28-8.27(m, 5H), 8.18-7.98(m, 7H),7.88-7.82(m, 6H), 7.52-7.41(m, 8H) 25 δ = 8.55(d, 1H), 8.45(d, 1H),8.30-8.21(m, 7H), 8.12- 7.98(m, 6H), 7.63-7.50(m, 12H), 7.46-7.25(m, 6H)28 δ = 8.81(d, 2H), 8.45(d, 1H), 8.28-8.24(m, 4H), 8.12(d, 1H),8.03-7.98(m, 2H), 7.89-7.81(m, 5H), 7.66(d, 2H), 7.52-7.32(m, 15H) 33 δ= 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.45(d, 1H), 8.28-8.12(m, 8H),8.04-7.98(m, 3H), 7.90-7.82(m, 7H), 7.52-7.41(m, 8H) 51 δ = 8.81(d, 2H),8.55(d, 1H), 8.45(d, 1H), 8.28(d, 2H), 8.21(d, 1H), 8.12(d, 1H), 8.04(d,1H), 7.98-7.88(m, 5H), 7.79(d, 2H), 7.68-7.63(m, 3H), 7.52-7.25(m, 14H)56 δ = 8.81(d, 2H), 8.45-8.41(m, 3H), 8.28-8.20(m, 5H), 8.04(d, 1H),7.98(d 2H), 7.90(s, 1H), 7.88(d, 2H), 7.70(s, 1H), 7.58-7.41(m, 15H) 57δ = 8.81(d, 2H), 8.45(d, 1H), 8.28-8.21(m, 5H), 8.04(d, 1H),7.98-7.85(m, 8H), 7.75(d, 1H), 7.64(d, 2H), 7.52- 7.32(m, 12H) 59 δ =8.81(d, 2H), 8.45(d, 1H), 8.28(d, 4H), 8.03-7.88(m, 9H), 7.73(d, 1H),7.59-7.41(m, 11H) 68 δ = 8.81(d, 2H), 8.45(d, 1H), 8.28(d, 2H),8.03-7.81(m, 13H), 7.66(d, 1H), 7.52-7.25(m, 13H) 69 δ = 8.45-8.41(m,3H), 8.30-8.21(m, 5H), 8.03-7.94(m, 5H), 7.80(d, 1H), 7.60-7.41(m, 14H),7.25(dd, 4H) 72 δ = 8.81(d, 2H), 8.45(d, 1H), 8.33-8.21(m, 6H), 8.00(d,2H), 7.89(d, 1H), 7.79-7.75(m, 3H), 7.66-7.62(m, 3H), 7.52-7.41(m, 11H),7.25(d, 4H) 75 δ = 8.81(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.33-8.21(m,6H), 8.12(d, 1H), 8.02-7.94(m, 3H), 7.79(d, 2H), 7.68- 7.63(m, 4H),7.52-7.19(m, 14H) 78 δ = 8.81(d, 2H), 8.45(d, 1H), 8.33-8.21(m, 6H),8.00(d, 2H), 7.89-7.57(m, 7H), 7.52-7.38(m, 12H), 7.19(d, 2H) 83 δ =9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.45(d, 1H), 8.28-8.12(m, 10H),8.04-7.98(m, 3H), 7.88-7.79(m, 6H), 7.52-7.41(m, 8H) 89 δ = 8.81(d, 2H),8.55(d, 1H), 8.45(d, 1H), 8.33-8.21(m, 6H), 8.12(d, 2H), 8.03-7.94(m,3H), 7.79(d, 2H), 7.68- 7.63(m, 3H), 7.52-7.25(m, 14H) 91 δ = 8.45(d,1H), 8.28-8.23(m, 6H), 8.12(d, 1H), 8.00(dd, 2H), 7.89(d, 1H), 7.81(d,2H), 7.72-7.32(m, 20H) 98 δ = 8.81(d, 2H), 8.45(d, 1H), 8.33-8.21(m,6H), 8.01(d, 2H), 7.90(s, 1H), 7.79-7.75(m, 3H), 7.64(d, 2H), 7.52-7.32(m, 11H), 7.25(d, 4H) 100 δ = 8.81(d, 2H), 8.45(d, 1H), 8.33-8.21(m,8H), 8.01(d, 2H), 7.90-7.85(m, 3H), 7.70(s, 1H), 7.52-7.41(m, 18H) 103 δ= 8.81(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.33-8.21(m, 6H), 8.12(d, 2H),8.03-7.90(m, 4H), 7.79(d, 2H), 7.68- 7.63(m, 3H), 7.52-7.25(m, 14H) 106δ = 8.81(d, 2H), 8.45(d, 1H), 8.33-8.21(m, 8H), 8.04(d, 1H), 7.98(d,1H), 7.90-7.85(m, 4H), 7.66(d, 1H), 7.52- 7.32 (m, 13H), 7.25(d, 2H) 112δ = 8.81(d, 2H), 8.45(d, 1H), 8.33-8.23(m, 5H), 8.03- 7.89(m, 5H),7.79-7.75(m, 3H), 7.64(d, 2H), 7.52- 7.25(m, 15H) 117 δ = 8.81(d, 2H),8.55(d, 1H), 8.45(d, 1H), 8.33-8.23(m, 5H), 8.12(d, 1H), 8.03-7.94(m,5H), 7.79(d, 2H), 7.68- 7.63(m, 3H), 7.52-7.25(m, 12H) 119 δ = 8.81(d,2H), 8.45(d, 1H), 8.33-8.23(m, 5H), 8.03- 7.66(m, 12H), 7.52-7.32(m,13H) 124 δ = 8.81(d, 2H), 8.45(d, 1H), 8.30-8.23(m, 7H), 8.03- 7.79(m,12H), 7.52-7.41(m, 13H) 125 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H),8.45(d, 1H), 8.23-8.12(m, 5H), 8.04-7.98(m, 2H), 7.88-7.79(m, 10H),7.66(t, 1H), 7.52-7.41(m, 8H) 130 δ = 8.81(d, 2H), 8.55(d, 1H), 8.45(d,1H), 8.23(s, 1H), 8.21(d, 1H), 8.12(d, 1H), 8.02-7.88(m, 5H), 7.79(d,4H), 7.68-7.63(m, 3H), 7.52-7.19(m, 14H) 134 δ = 8.45-8.41(m, 3H),8.30-8.21(m, 5H), 8.02-7.98(m, 3H), 7.80-7.79(m, 3H), 7.66-7.41(m, 15H),7.52(d, 4H) 138 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.45(d, 1H),8.27-8.12(m, 6H), 8.04-7.98(m, 3H), 7.88-7.79(m, 10H), 7.52-7.41(m, 8H)143 δ = 8.81(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.27(s, 1H), 8.23(s, 1H),8.21(d, 1H), 8.12(d, 2H), 8.03-7.88(m, 5H), 7.79(d, 4H), 7.68-7.63(m,3H), 7.52-7.19(m, 14H) 149 δ = 8.81(d, 2H), 8.45(d, 1H), 8.27(s, 1H),8.23(s, 1H), 8.01(d, 2H), 7.89-7.79(m, 11H), 7.66(d, 1H), 7.52- 7.25(m,13H) 151 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.45(d, 1H),8.23-8.12(m, 5H), 8.04-7.98(m, 3H), 7.88-7.79(m, 11H), 7.52-7.41(m, 8H)156 δ = 8.81(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.23(s, 1H), 8.21(d, 1H),8.12(d, 1H), 8.04-7.88(m, 6H), 7.79(d, 4H), 7.68-7.63(m, 3H),7.52-7.25(m, 14H) 159 δ = 8.81(d, 2H), 8.45(d, 1H), 8.30(d, 2H), 8.22(d,2H), 8.01(d, 2H), 7.90-7.79(m, 8H), 7.66(d, 1H), 7.52-7.25 (m, 15H) 166δ = 8.81(d, 2H), 8.45(d, 1H), 8.23(s, 1H), 8.03-7.79(m, 12H), 7.64(d,2H), 7.52-7.32 (m, 15H) 171 δ = 8.55(d, 1H), 8.45(d, 1H), 8.30-8.21(m,4H), 8.12- 7.94(m, 7H), 7.79(d, 5H), 7.52-7.25(m, 14H) 174 δ =8.45-8.41(m, 3H), 8.30-8.21(m, 4H), 8.03-7.94(m, 5H), 7.80-7.79(m, 3H),7.60-7.41(m, 13H), 7.52(d, 4H) 178 δ = 8.45(d, 1H), 8.30-8.21(m, 7H),8.03-7.94(m, 4H), 7.85-7.79(m, 8H), 7.60-7.41(m, 17H), 7.52(d, 2H) 179 δ= 9.30(d, 2H), 9.15(s, 2H), 8.81(d, 2H), 8.53(d, 2H), 8.45(d, 1H),8.21(d, 1H), 8.00(dd, 2H), 7.89-7.81(m, 5H), 7.70-7.66(m, 4H), 7.51(td,2H), 7.38-7.25(m, 7H), 7.14(t, 2H) 182 δ = 9.30(d, 2H), 9.15(s, 2H),8.81(d, 2H), 8.53(d, 2H), 8.45(d, 1H), 8.21(d, 1H), 8.02-7.88(m, 7H),7.73- 7.48(m, 13H), 7.14(t, 2H) 186 δ = 9.30(d, 2H), 9.15(s, 2H),8.81(d, 2H), 8.53(d, 2H), 8.45(d, 1H), 8.27(d, 1H), 8.12(d, 1H),8.03-7.98(m, 5H), 7.87(dd, 3H), 7.70(t, 3H), 7.57-7.48(m, 7H), 7.14(t,2H) 190 δ = 9.30(d, 2H), 9.15(s, 2H), 8.81(d, 2H), 8.53(d, 2H), 8.45(d,1H), 8.21(d, 1H), 8.04-7.88(m, 8H), 7.73- 7.48(m, 12H), 7.14(t, 2H) 197δ = 8.93(d, 2H), 8.45(d, 1H), 8.26-8.21(m, 3H), 8.12(d, 2H),8.02-7.77(m, 15H), 7.66-7.45(m, 11H) 199 δ = 8.81(d, 2H), 8.45(d, 1H),8.27(s, 1H), 8.12(d, 1H), 8.03-7.98(m, 2H), 7.89-7.75(m, 12H), 7.64(d,2H), 7.52-7.32(m, 11H) 203 δ = 8.81(d, 2H), 8.45(d, 1H), 8.21(d, 1H),8.04-7.98(m, 2H), 7.89-7.75(m, 12H), 7.64(d, 2H), 7.52-7.32 (m, 11H) 207δ = 8.81(d, 2H), 8.45(d, 1H), 8.04-7.77(m, 16H), 7.64(d, 2H), 7.52-7.32(m, 11H) 212 δ = 8.55(d, 1H), 8.45(d, 1H), 8.30-8.21(m, 5H), 8.12(d,1H), 8.02-7.94(m, 3H), 7.85-7.79(dd, 4H), 7.68- 7.65(m, 4H),7.54-7.25(m, 14H) 217 δ = 8.45-8.41(m, 3H), 8.30-8.20(m, 7H), 8.12(d,1H), 8.03-7.98(m, 3H), 7.85(d, 2H), 7.70(s, 1H), 7.58- 7.48(m, 13H),7.25(d, 2H) 219 δ = 8.45(d, 1H), 8.30-8.21(m, 7H), 8.01(d, 2H), 7.90-7.85(m, 3H), 7.54-7.41(m, 11H), 7.25(d, 2H) 223 δ = 8.45(d, 1H),8.30-8.28(m, 6H), 8.03-7.94(m, 4H), 7.85(d, 2H), 7.54-7.41(m, 11H),7.25(d, 2H) 228 δ = 8.55(d, 1H), 8.45(d, 1H), 8.30-8.21(m, 8H), 8.12(d,1H), 8.02-7.94(m, 3H), 7.79(d, 2H), 7.68-7.63(m, 4H), 7.54-7.25(m, 14H)231 δ = 8.45(d, 1H), 8.30-8.23(m, 8H), 8.12(d, 1H), 8.03- 7.98(m, 2H),7.85-7.799(m, 4H), 7.54-7.41(m, 11H) 233 δ = 8.45-8.41(m, 3H),8.30-8.20(m, 11H), 8.12(d, 1H), 8.03-7.98(m, 3H), 7.85(d, 2H),7.58-7.48(m, 11H), 7.25(d, 2H) 236 δ = 8.55(d, 1H), 8.45(d, 1H),8.30-8.21(m, 8H), 8.12(d, 1H), 8.04(d, 1H), 7.98-7.79(m, 7H),7.68-7.63(m, 3H), 7.54-7.25(m, 12H) 243 δ = 8.45(d, 1H), 8.30(d, 6H),8.22(d, 2H), 8.02-7.98(d, 2H), 7.85(d, 6H), 7.66(d, 1H), 7.54-7.41(m,15H), 7.25(d, 2H) 252 δ = 8.55(d, 1H), 8.45(d, 1H), 8.30(d, 2H), 8.22(d,2H), 8.12(d, 1H), 8.04-7.79(m, 10H), 7.68-7.63(m, 4H), 7.54-7.25(m, 14H)253 δ = 8.45-8.41(m, 3H), 8.30-8.20(m, 8H), 8.04-7.98(m, 3H), 7.90(s,1H), 7.79(d, 2H), 7.70(s, 1H), 7.58- 7.48(m, 13H), 7.25(d, 2H) 256 δ =8.55(d, 1H), 8.45(d, 1H), 8.30(d, 2H), 8.23(s, 1H), 8.12(d, 1H),8.03-7.94(m, 5H), 7.85-7.79(m, 6H), 7.68-7.63(m, 3H), 7.54-7.25(m, 14H)259 δ = 9.30(d, 2H), 9.15(s, 2H), 8.81(d, 2H), 8.53(d, 2H), 8.45(d, 1H),8.30(d, 2H), 8.21(d, 1H), 8.02-7.98(m, 2H), 7.70(t, 3H), 7.54-7.50(m,5H), 7.25(d, 4H), 7.14(t, 2H) 263 δ = 9.30(d, 2H), 9.15(s, 2H), 8.53(d,2H), 8.45(d, 1H), 8.30(d, 2H), 8.27(s, 1H), 8.12(s, 1H), 8.02-7.98(m,2H), 7.70(t, 3H), 7.57-7.48(m, 8H), 7.14(t, 2H) 265 δ = 9.30(d, 2H),9.15(s, 2H), 8.53(d, 2H), 8.45(d, 1H), 8.30(d, 2H), 8.21(d, 1H),8.04-7.98(m, 2H), 7.90(s, 1H), 7.70(t, 2H), 7.57-7.50(m, 5H), 7.25(d,4H), 7.14(t, 2H) 272 δ = 8.45(d, 1H), 8.30(d, 2H), 8.21(d, 1H),8.02-7.98(m, 2H), 7.83-7.77(m, 8H), 7.66(t, 1H), 7.54-7.45(m, 11H),7.25(d, 4H) 278 δ = 8.45(d, 1H), 8.30(d, 2H), 8.21(d, 1H), 8.04-7.98(m,2H), 7.90(s, 1H), 7.83-7.77(m, 8H), 7.54-7.45(m, 11H), 7.25(d, 4H) 283 δ= 8.55(d, 1H), 8.45(d, 2H), 8.28(d, 4H), 8.21(d, 1H), 8.10-7.94(m, 4H),7.85(d, 2H), 7.66-7.41(m, 12H), 7.25(d, 2H) 288 δ = 8.55(d, 1H), 8.45(d,2H), 8.28(d, 3H), 8.12-7.94(m, 5H), 7.85-7.79(m, 4H), 7.68-7.63(m, 4H),7.55-7.25(m, 13H) 293 δ = 8.55(d, 1H), 8.46(d, 2H), 8.28-8.21(m, 4H),8.10- 7.98(m, 5H), 7.90-7.81(m, 6H), 7.70-7.32(m, 15H), 7.25(m, 2H) 295δ = 8.55(d, 1H), 8.46(d, 2H), 8.28(d, 4H), 8.10-7.94(m, 6H), 7.64(t,1H), 7.55-7.41(m, 10H), 7.25(d, 2H) 305 δ = 8.55(d, 1H), 8.46(d, 2H),8.30-8.20(m, 9H), 8.12- 7.98(m, 5H), 7.85(d, 2H), 7.64-7.41(m, 11H),7.25(d, 2H) 308 δ = 8.55(d, 2H), 8.46(d, 2H), 8.30-8.21(m, 6H), 8.12-7.90(m, 7H), 7.85-7.79(m, 4H), 7.64-7.25(m, 15H) 319 δ = 8.55(d, 1H),8.46(d, 2H), 8.27(s, 1H), 8.23(s, 1H), 8.12-7.98(m, 5H), 7.85-7.79(m,4H), 7.64-7.41(m, 11H), 7.25(d, 2H) 324 δ = 8.55(d, 2H), 8.46(d, 2H),8.23(s, 1H), 8.21(s, 1H), 8.12-7.79(m, 13H), 7.68(d, 2H), 7.64-7.25(m,17H) 328 δ = 8.55(d, 2H), 8.46(d, 2H), 8.23(s, 1H), 8.12-7.94(m, 9H),7.85-7.79(m, 6H), 7.68(d, 2H), 7.64-7.25(m, 15H) 334 δ = 9.30(d, 2H),9.15(s, 2H), 8.55-8.45(m, 5H), 8.27(s, 1H), 8.12-7.98(m, 5H),7.70-7.50(m, 7H), 7.25(d, 4H), 7.14(t, 2H) 347 δ = 8.55(d, 1H), 8.46(d,2H), 8.27(s, 1H), 8.12-7.98(m, 5H), 7.83-7.79(m, 8H), 7.64(t, 1H),7.55-7.45(m, 10H), 7.25(d, 4H) 352 δ = 8.55(d, 1H), 8.46(d, 2H),8.12-7.94(m, 6H), 7.79- 7.77(m, 8H), 7.64(t, 1H), 7.55-7.45(m, 10H) 358δ = 8.93(d, 2H), 8.44(d, 2H), 8.28(d, 3H), 8.12(d, 3H), 8.03-7.98(m,2H), 7.88-7.82(m, 8H), 7.52-7.41(m, 10H), 7.25(d, 4H) 367 δ = 8.93(d,2H), 8.45(d, 2H), 8.28-8.21(m, 4H), 8.12(d, 2H), 8.04-7.98(m, 2H),7.90-7.70(m, 9H), 7.52-7.41(m, 10H) 373 δ = 8.93(d, 2H), 8.45(d, 2H),8.27(s, 1H), 8.23(s, 1H), 8.12(d, 3H), 8.03-7.98(m, 2H), 7.88-7.79(m,10H), 7.70(s, 1H), 7.57-7.41(m, 11H), 7.25(d, 2H) 379 δ = 9.30(d, 2H),9.15(s, 2H), 8.93(d, 2H), 8.53-8.44(m, 4H), 8.21(d, 1H), 8.12(d, 2H),8.02-7.98(m, 2H), 7.88- 7.82(m, 4H), 7.70-7.66(m, 3H), 7.51(dd, 2H),7.25(d, 4H), 7.14(t, 2H) 382 δ = 9.30(d, 2H), 9.15(s, 2H), 8.93(d, 2H),8.53-8.44(m, 4H), 8.27(s, 1H), 8.12(d, 3H), 8.02-7.98(m, 2H), 7.88-7.82(m, 4H), 7.70(t, 4H), 7.57-7.48(m, 8H), 7.14(t, 2H) 389 δ = 8.93(d,2H), 8.44(d, 2H), 8.27(s, 1H), 8.12(d, 3H), 8.03-7.98(m, 2H),7.88-7.77(m, 12H), 7.52-7.45(m, 8H) 393 δ = 8.93(d, 2H), 8.44(d, 2H),8.12(d, 2H), 8.03-7.77(m, 16H), 7.52-7.45(m, 8H) 397 δ = 9.66(s, 1H),8.93(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.28-8.21(m, 6H), 8.12(d, 3H),8.03-7.98(m, 2H), 7.88-7.82(m, 6H), 7.52-7.41(m, 8H), 7.25(d, 2H) 406 δ= 9.66(s, 1H), 8.93(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.28-8.21(m, 4H),8.12(d, 2H), 8.03-7.70(m, 12H), 7.52-7.41(m, 10H) 415 δ = 9.66(s, 1H),9.30(d, 2H), 9.15(s, 2H), 8.93(d, 2H), 8.54(d, 3H), 8.45(d, 1H),8.21-7.82(m, 11H), 7.70(t, 3H), 7.57-7.48(m, 5H), 7.14(t, 2H) 419 δ =9.66(s, 1H), 8.93(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.21(d, 2H), 8.12(d,2H), 8.04-7.98(m, 2H), 7.88- 7.77(m, 11H), 7.52-7.45(m, 10H) 423 δ =8.81(d, 2H), 8.48(dd, 2H), 8.28-8.16(m, 4H), 8.06- 7.81(m, 8H),7.70-7.32(m, 14H) 425 δ = 8.81(d, 2H), 8.48(dd, 2H), 8.33-8.23(m, 7H),8.16(d, 1H), 8.06(d, 1H), 7.98(d, 1H), 7.85-7.81(m, 3H), 7.67(t, 2H),7.52-7.41(m, 10H) 433 δ = 9.30(d, 2H), 9.15(s, 2H), 8.81(d, 2H),8.53-8.45(m, 4H), 8.16(d, 1H), 8.06(d, 1H), 7.98(d, 1H), 7.88- 7.81(m,3H), 7.70-7.67(m, 4H), 7.52-7.50(m, 2H), 7.25(d, 4H), 7.14(t, 2H) 435 δ= 8.81(d, 2H), 8.45(d, 1H), 8.28(d, 4H), 8.16(d, 2H), 8.05(s, 1H),7.98(d, 1H), 7.88(d, 2H), 7.68-7.67(t, 2H), 7.52-7.41(m, 8H) 441 δ =8.81(d, 2H), 8.45-8.41(m, 3H), 8.33-8.16(m, 10H), 7.98(d, 1H), 7.67(t,3H), 7.58-7.41(m, 8H), 7.25(d, 2H) 444 δ = 8.81(d, 2H), 8.45(d, 1H),8.23(s, 1H), 8.16(d, 2H), 8.05(s, 1H), 7.98(d, 1H), 7.89-7.67(m, 13H),7.57- 7.32(m, 10H) 453 δ = 8.81(d, 2H), 8.54(d, 1H), 8.45(d, 2H),8.41-8.16(m, 10H), 7.98(d, 4H), 7.67(t, 2H), 7.58-7.41(m, 8H), 7.25(d,2H) 455 δ = 8.81(d, 2H), 8.54(d, 1H), 8.45(d, 2H), 8.30(d, 4H), 8.23(s,1H), 8.16(d, 1H), 7.98(d, 3H), 7.88-7.85(m, 6H), 7.67(t, 2H),7.52-7.41(m, 12H) 460 δ = 8.81(d, 2H), 8.54(d, 1H), 8.45(d, 1H), 8.16(d,1H), 7.98(d, 3H), 7.88(d, 2H), 7.77-7.67(m, 8H), 7.52- 7.45(m, 10H) 461δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.28-8.18(m, 6H),8.12-8.02(m, 4H), 7.88-7.82(m, 7H), 7.66(t, 2H), 7.51-7.32(m, 8H) 467 δ= 8.81(d, 2H), 8.55(d, 1H), 8.28(d, 2H), 8.21(d, 1H), 8.12(d, 1H),8.02(d, 1H), 7.94-7.79(m, 6H), 7.68- 7.63(m, 5H), 7.50-7.19(m, 14H) 470δ = 8.81(d, 2H), 8.28(d, 2H), 8.21(d, 1H), 8.02(d, 1H), 7.89-7.85(m,8H), 7.66(td, 3H), 7.51-7.19(m, 15H) 474 δ = 8.81(d, 2H), 8.28(d, 4H),8.21(d, 1H), 8.02(d, 1H), 7.89-7.85(m, 8H), 7.66(t, 3H), 7.51-7.25(m,13H) 477 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.28(d, 5H),8.18-8.03(m, 6H), 7.89-7.82(m, 7H), 7.66(d, 1H), 7.51-7.32(m, 8H) 485 δ= 8.55(d, 1H), 8.30-8.21(m, 7H), 8.12-8.03(m, 4H), 7.91(d, 2H),7.66-7.60(m, 3H), 7.52-7.25(m, 16H) 488 δ = 8.81(d, 2H), 8.28-8.24(m,4H), 8.12(d, 1H), 8.03(d, 1H), 7.89-7.85(m, 6H), 7.68(t, 3H),7.57-7.32(m, 15H) 493 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H),8.28-8.04(m, 10H), 7.90-7.82(m, 8H), 7.66(d, 1H), 7.51-7.32(m, 8H) 511 δ= 8.81(d, 2H), 8.55(d, 1H), 8.28(d, 2H), 8.21(d, 1H), 8.12(d, 1H),8.04(d, 1H), 7.94-7.88(m, 5H), 7.79(d, 2H), 7.68-7.63(m, 4H),7.51-7.25(m, 14H) 516 δ = 8.81(d, 2H), 8.43(d, 2H), 8.28-8.20(m, 5H),8.01(d, 2H), 7.90-7.88(m, 4H), 7.70-7.32(m, 17H) 517 δ = 8.81(5, 2H),8.28-8.21(m, 5H), 8.04(d, 1H), 7.95- 7.85(m, 8H), 7.75(d, 1H), 7.64(d,3H), 7.51-7.25(m, 12H) 519 δ = 8.81(d, 2H), 8.28(d, 4H), 8.03-7.88(m,9H), 7.73- 7.32(m, 13H) 528 δ = 8.81(d, 2H), 8.28(d, 2H), 8.03-7.79(m,13H), 7.66(d, 1H), 7.52-7.25(m, 13H) 529 δ = 8.45-8.41(m, 2H),8.30-8.21(m, 5H), 8.03-7.89(m, 5H), 7.80(d, 1H), 7.66-7.50(m, 11H),7.41-7.25(m, 6H) 532 δ = 8.81(d, 2H), 8.33-8.21(m, 6H), 8.02(d, 1H),7.89(d, 2H), 7.79-7.75(m, 3H), 7.66-7.62(m, 4H), 7.51- 7.25(d, 14H) 535δ = 8.81(d, 2H), 8.55(d, 1H), 8.33-8.21(m, 6H), 8.12(d, 1H), 8.02(d,1H), 7.94-7.89(m, 2H), 7.79(d, 2H), 7.68- 7.63(m, 5H), 7.51-7.19(m, 14H)538 δ = 8.81(d, 2H), 8.33-8.21(m, 6H), 8.02(d, 1H), 7.89- 7.57(m, 10H),7.51-7.32(m, 12H), 7.19(d, 2H) 543 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d,2H), 8.33-8.12(m, 10H), 8.04(d, 2H), 7.89-7.79(m, 7H), 7.66(d, 1H),7.51-7.32(m, 8H) 549 δ = 8.81(d, 2H), 8.55(d, 1H), 8.33-8.21(m, 6H),8.12(d, 2H), 8.03(d, 1H), 7.94-7.89(m, 2H), 7.79(d, 2H), 7.68- 7.63(m,4H), 7.52-7.25(m, 14H) 551 δ = 8.28-8.23(m, 6H), 8.12(d, 1H), 8.03(d,1H), 7.89(d, 2H), 7.81(d, 2H), 7.72-7.32(m, 21H) 558 δ = 8.81(d, 2H),8.33-8.21(m, 6H), 8.04(d, 1H), 7.90(s, 1H), 7.89(d, 2H), 7.79-7.75(m,3H), 7.64(d, 3H), 7.51- 7.32(m, 11H), 7.25(d, 4H) 560 δ = 8.81(d, 2H),8.33-8.21(m, 8H), 8.04(d, 1H), 7.90- 7.85(m, 4H), 7.70(s, 1H), 7.66(d,1H), 7.52-7.32(m, 18H) 563 δ = 8.81(d, 2H), 8.55(d, 1H), 8.33-8.21(m,6H), 8.12(d, 2H), 8.04-7.90(m, 4H), 7.79(d, 2H), 7.68-7.63(m, 3H),7.52-7.25(m, 14H) 566 δ = 8.81(d, 2H), 8.33-8.21(m, 8H), 8.04(d, 1H),7.90- 7.81(m, 5H), 7.66(d, 1H), 7.52-7.32 (m, 15H) 572 δ = 8.81(d, 2H),8.33-8.23(m, 5H), 8.03-7.89(m, 5H), 7.79-7.75(m, 3H), 7.64(d, 2H),7.52-7.25(m, 15H) 577 δ = 8.81(d, 2H), 8.55(d, 1H), 8.33-8.23(m, 5H),8.12(d, 1H), 8.03-7.94(m, 5H), 7.79(d, 2H), 7.68-7.63(m, 4H),7.52-7.25(m, 12H) 579 δ = 8.81(d, 2H), 8.33-8.23(m, 5H), 8.03-7.66(m,12H), 7.52-7.32(m, 13H) 584 δ = 8.81(d, 2H), 8.30-8.23(m, 7H),8.03-7.79(m, 12H), 7.66(d, 1H), 7.52-7.32(m, 13H) 585 δ = 9.15(s, 1H),8.93(d, 2H), 8.81(d, 2H), 8.23-8.02(m, 7H), 7.88-7.79(m, 11H), 7.66(t,2H), 7.51-7.32(m, 8H) 590 δ = 8.81(d, 2H), 8.55(d, 1H), 8.23(s, 1H),8.21(d, 1H), 8.12(d, 1H), 8.02(d, 1H), 7.89-7.79(m, 8H), 7.68- 7.63(m,5H), 7.51-7.19(m, 14H) 594 δ = 8.45-8.41(m, 2H), 8.30-8.21(m, 5H),8.00(d, 2H), 7.89(d, 1H), 7.80(d, 3H), 7.66-7.32(m, 16H), 7.25(d, 4H)598 δ = 9.15(s, 1H), 8.93(d, 2H), 8.81(d, 2H), 8.27-8.03(m, 8H),7.88-7.79(m, 11H), 7.66(d, 1H), 7.51-7.32(m, 8H) 603 δ = 8.81(d, 2H),8.55(d, 1H), 8.27(s, 1H), 8.23(s, 1H), 8.12(d, 2H), 8.03(d, 1H),7.94-7.88(m, 4H), 7.79(d, 4H), 7.68-7.63(m, 4H), 7.52-7.29(m, 14H) 609 δ= 8.81(d, 2H), 8.27(s, 1H), 8.23(s, 1H), 8.12(d, 1H), 8.03(d, 1H),7.89-7.79(m, 12H), 7.66(d, 1H), 7.51- 7.25(m, 13H) 611 δ = 9.15(s, 1H),8.93(d, 2H), 8.81(d, 2H), 8.23-8.04(m, 7H), 7.90-7. 7.79(m, 12H),7.66(d, 1H), 7.51-7.32(m, 8H) 616 δ = 8.81(d, 2H), 8.55(d, 1H), 8.23(s,1H), 8.21(d, 1H), 8.12(d, 1H), 8.04(d, 1H), 7.94-7.88(m, 5H), 7.79(d,4H), 7.68-7.63(m, 4H), 7.52-7.25(m, 14H) 619 δ = 8.81(d, 2H), 8.30(d,2H), 8.23(s, 1H), 8.21(d, 1H), 8.04(d, 1H), 7.90-7.79(m, 9H), 7.66(d,2H), 7.52-7.25 (m, 15H) 626 δ = 8.81(d, 2H), 8.23(s, 1H), 8.03-7.79(m,12H), 7.64(d, 3H), 7.52-7.32(m, 11H), 7.25(d, 4H) 631 δ = 8.55(d, 1H),8.30-8.21(m, 4H), 8.12-7.89(m, 7H), 7.79(d, 5H), 7.66-7.25(m, 17H) 634 δ= 8.45-8.41(m, 3H), 8.30-8.23(m, 4H), 8.03-7.89(m, 5H), 7.80-7.79(m,3H), 7.66-7.32(m, 15H), 7.25(d, 4H) 638 δ = 8.30-8.21(m, 7H), 8.03(d,1H), 7.95-7.79(m, 11H), 7.60-7.32(m, 20H), 7.52(d, 2H) 639 δ = 9.30(d,2H), 9.15(s, 2H), 8.81(d, 2H), 8.53(d, 2H), 8.21(d, 1H), 8.02(d, 1H),7.89-7.81(m, 6H), 7.70- 7.66(m, 4H), 7.38-7.25(m, 9H), 7.14(t, 2H) 642 δ= 9.30(d, 2H), 9.15(s, 2H), 8.81(d, 2H), 8.53(d, 2H), 8.21(d, 1H),8.02-7.88(m, 7H), 7.73-7.48(m, 12H), 7.38-7.32(m, 2H), 7.14(t, 2H) 646 δ= 9.30(d, 2H), 9.15(s, 2H), 8.81(d, 2H), 8.53(d, 2H), 8.45(d, 1H),8.27(s, 1H), 8.12(d, 1H), 8.03-7.98(m, 8H), 7.70-7.48(m, 9H), 7.38(t,1H), 7.32(t, 1H), 7.14(t, 2H) 650 δ = 9.30(d, 2H), 9.15(s, 2H), 8.81(d,2H), 8.53(d, 2H), 8.21(d, 1H), 8.04-7.88(m, 8H), 7.73-7.48(m, 11H),7.38(t, 1H), 7.32(t, 1H), 7.14(t, 2H) 657 δ = 8.93(d, 2H), 8.45(d, 1H),8.26-8.21(m, 3H), 8.12(d, 2H), 8.02(d, 1H), 7.93-7.77(m, 14H),7.66-7.32(m, 12H) 659 δ = 8.81(d, 2H), 8.27(s, 1H), 8.12(d, 1H), 8.03(d,1H), 7.89-7.75(m, 13H), 7.64(d, 3H), 7.45-7.32 (m, 11H) 663 δ = 8.81(d,2H), 8.21(d, 1H), 8.04(d, 1H), 7.90-7.77(m, 12H), 7.66(d, 1H),7.52-7.32(m, 13H) 667 δ = 8.81(d, 2H), 8.03-7.77(m, 16H), 7.64(d, 3H),7.45- 7.32 (m, 11H) 672 δ = 8.55(d, 1H), 8.30-8.21(m, 5H), 8.12(d, 1H),8.02(d, 1H), 7.94-7.79(m, 6H), 7.68-7.63(m, 5H), 7.54-7.25(m, 14H) 677 δ= 8.45-8.41(m, 2H), 8.30-8.20(m, 7H), 8.12(d, 1H), 8.01(d, 2H),7.89-7.85(m, 3H), 7.70-7.32(m, 15H), 7.25(d, 2H) 679 δ = 8.30-8.21(m,7H), 8.04(d, 1H), 7.90-7.85(m, 4H), 7.66(d, 1H), 7.54-7.32(m, 11H),7.25(d, 2H) 683 δ = 8.30-8.28(m, 6H), 8.03-7.85(m, 6H), 7.66(d, 1H),7.54-7.32(m, 11H), 7.25(d, 2H) 688 δ = 8.55(d, 1H), 8.30-8.21(m, 8H),8.12(d, 1H), 8.02(d, 1H), 7.91(d, 2H), 7.79(d, 2H), 7.68-7.63(m, 5H),7.54- 7.25(m, 14H) 691 δ = 8.30-8.23(m, 8H), 8.12(d, 1H), 8.03(d, 1H),7.89- 7.79(m, 5H), 7.66(d, 1H), 7.54-7.32(m, 11H) 693 δ = 8.45-8.41(m,2H), 8.30-8.20(m, 11H), 8.12(d, 1H), 8.01(d, 2H), 7.89-7.85(m, 3H),7.58-7.48(m, 12H), 7.25(d, 2H) 696 δ = 8.55(d, 1H), 8.30-8.21(m, 8H),8.12(d, 1H), 8.04(d, 1H), 7.94-7.79(m, 7H), 7.68-7.63(m, 4H),7.54-7.25(m, 12H) 703 δ = 8.30(d, 6H), 8.22(d, 2H), 8.02(d, 1H),7.89-7.85(m, 7H), 7.66(t, 2H), 7.54-7.32(m, 15H), 7.25(d, 2H) 712 δ =8.55(d, 1H), 8.30-8.21(m, 4H), 8.12(d, 1H), 8.04(d, 1H), 7.94-7.79(m,9H), 7.68-7.63(m, 4H), 7.54-7.25(m, 14H) 713 δ = 8.45-8.41(m, 2H),8.30-8.20(m, 8H), 8.04-7.98(m, 2H), 7.90(s, 1H), 7.89(d, 1H), 7.79(d,2H), 7.70(s, 1H), 7.66-7.32(m, 14H), 7.25(d, 2H) 716 δ = 8.55(d, 1H),8.30(d, 2H), 8.23(s, 1H), 8.12(d, 1H), 8.03-7.79(m, 11H), 7.68-7.63(m,4H), 7.54-7.25(m, 14H) 719 δ = 9.30(d, 2H), 9.15(s, 2H), 8.53(d, 2H),8.30(d, 2H), 8.21(d, 1H), 8.02(d, 1H), 7.98(d, 1H), 7.68(td, 4H),7.54-7.32(m, 5H), 7.25(d, 4H), 7.14(t, 2H) 723 δ = 9.30(d, 2H), 9.15(s,2H), 8.53(d, 2H), 8.30(d, 2H), 8.27(s, 1H), 8.12(d, 1H), 8.03(d, 1H),7.98(d, 1H), 7.70(t, 3H), 7.57-7.32(m, 9H), 7.14(t, 2H) 725 δ = 9.30(d,2H), 9.15(s, 2H), 8.53(d, 2H), 8.30(d, 2H), 8.21(d, 1H), 8.04(d, 1H),7.90(d, 2H), 7.70(t, 2H), 7.66(d, 1H), 7.54-7.32(m, 5H), 7.25(d, 4H),7.14(t, 2H) 732 δ = 8.30(d, 2H), 8.21(d, 1H), 8.02(d, 1H), 7.89-7.77(m,9H), 7.66(t, 2H), 7.54-7.32(m, 11H), 7.25(d, 4H) 738 δ = 8.30(d, 2H),8.21(d, 1H), 8.04(d, 1H), 7.89-7.77(m, 10H), 7.66(d, 1H), 7.54-7.32(m,11H), 7.25(d, 4H) 743 δ = 8.55(d, 1H), 8.46(d, 1H), 8.28-8.21(m, 5H),8.10- 8.02(m, 3H), 7.89-7.85(m, 3H), 7.65(t, 3H), 7.55- 7.32(m, 10),7.25(d, 2H) 748 δ = 8.55(d, 1H), 8.46(d, 11H), 8.28(d, 3H), 8.12-8.03(m, 5H), 7.94-7.79(m, 6H), 7.68-7.63(m, 5H), 7.55-7.25(m, 11H) 753 δ= 8.55(d, 1H), 8.46(d, 1H), 8.28-8.21(m, 4H), 8.10- 8.04(m, 3H),7.90-7.85(m, 7H), 7.70-7.32(m, 16H), 7.25(m, 2H) 755 δ = 8.55(d, 1H),8.46(d, 11H), 8.28(d, 4H), 8.10- 7.85(m, 8H), 7.66(d, 1H), 7.64(t, 1H),7.55-7.41(m, 10H), 7.25(d, 2H) 765 δ = 8.55(d, 1H), 8.46-8.41(m, 3H),8.30-8.20(m, 9H), 8.12-7.98(m, 5H), 7.89(d, 1H), 7.85(d, 2H), 7.66-7.32(m, 12H), 7.25(d, 2H) 768 δ = 8.55(d, 2H), 8.46(d, 1H), 8.30-8.21(m,6H), 8.12- 8.04(m, 4H), 7.94-7.79(m, 7H), 7.64-7.25(m, 16H) 779 δ =8.55(d, 1H), 8.46(d, 1H), 8.27(s, 1H), 8.23(s, 1H), 8.12-8.03(m, 4H),7.89-7.79(m, 7H), 7.66-7.32(m, 12H), 7.25(d, 2H) 784 δ = 8.55(d, 2H),8.46(d, 1H), 8.23(s, 1H), 8.21(s, 1H), 8.12-8.04(m, 4H), 7.94-7.79(m,9H), 7.68-7.64(m, 5H), 7.55-7.25(m, 13H) 788 δ = 8.55(d, 2H), 8.46(d,1H), 8.23(s, 1H), 8.12-7.94(m, 8H), 7.85-7.79(m, 6H), 7.68(d, 2H),7.64-7.25(m, 16H) 794 δ = 9.30(d, 2H), 9.15(s, 2H), 8.55-8.46(m, 4H),8.27(s, 1H), 8.12-8.03(m, 4H), 7.89(d, 1H), 7.70-7.55(m, 6H), 7.35(t,2H), 7.25(d, 4H), 7.14(t, 2H) 807 δ = 8.55(d, 1H), 8.46(d, 1H), 8.27(s,1H), 8.12-8.03(m, 4H), 7.89-7.77(m, 9H), 7.64-7.55(m, 4H), 7.45-7.32(m,8H), 7.25(d, 4H) 812 δ = 8.55(d, 1H), 8.46(d, 1H), 8.10-7.77(m, 14H),7.64- 7.55(m, 4H), 7.45-7.32(m, 8H) 818 δ = 8.93(d, 2H), 8.44(d, 1H),8.28(d, 3H), 8.12(d, 3H), 8.03(d, 1H), 7.89-7.82(m, 9H), 7.66(d, 1H),7.52- 7.32(m, 10H), 7.25(d, 4H) 827 δ = 8.93(d, 2H), 8.44(d, 1H),8.28-8.21(m, 4H), 8.12- 8.04(m, 3h), 7.90-7.66(m, 11H), 7.57-7.32(m,10H) 833 δ = 8.93(d, 2H), 8.44(d, 1H), 8.27(s, 1H), 8.23(s, 1H), 8.12(d,3H), 8.03(d, 1H), 7.89-7.79(m, 11H), 7.70(s, 1H), 7.66(d, 1H),7.57-7.32(m, 11H), 7.25(d, 2H) 839 δ = 9.30(d, 2H), 9.15(s, 2H), 8.93(d,2H), 8.53(d, 2H), 8.44(s, 1H), 8.21(d, 1H), 8.12(d, 2H), 8.02(d, 1H),7.89-7.82(m, 5H), 7.70-7.66(m, 4H), 7.38(t, 1H), 7.32(t, 1H), 7.25(d,4H), 7.14(t, 2H) 842 δ = 9.30(d, 2H), 9.15(s, 2H), 8.93(d, 2H), 8.53(d,2H), 8.44(s, 1H), 8.27(s, 1H), 8.12(d, 3H), 8.03(d, 1H), 7.89-7.82(m,5H), 7.70(t, 4H), 7.57-7.32(m, 8H9), 7.14(t, 2H) 849 δ = 8.93(d, 2H),8.44(s, 1H), 8.27(s, 1H), 8.12(d, 3H), 8.03(d, 1H), 7.89-7.77(m, 13H),7.66(d, 1H), 7.45- 7.32(m, 8H) 853 δ = 8.93(d, 2H), 8.44(s, 1H), 8.12(d,2H), 8.03-7.77(m, 15H), 7.66(d, 1H), 7.45-7.32(m, 8H) 857 δ = 9.66(s,1H), 8.93(d, 2H), 8.55(d, 1H), 8.28-8.21(m, 6H), 8.12(d, 3H), 8.03(m,1H), 7.89-7.82(m, 7H), 7.66(d, 1H), 7.51-7.25(m, 10H) 866 δ = 9.66(s,1H), 8.93(d, 2H), 8.55(d, 1H), 8.28-8.21(m, 4H), 8.12(d, 2H),8.03-7.70(m, 12H), 7.52-7.41(m, 10H) 875 δ = 9.66(s, 1H), 9.30(d, 2H),9.15(s, 2H), 8.93(d, 2H), 8.54(d, 3H), 8.21-8.04(m, 5H), 7.90-7.82(m,6H), 7.70(t, 3H), 7.66-7.32(m, 6H), 7.14(t, 2H) 879 δ = 9.66(s, 1H),8.93(d, 2H), 8.55(d, 1H), 8.45(d, 1H), 8.21(d, 2H), 8.12(d, 2H), 8.04(d,1H), 7.89-7.77(m, 13H), 7.52-7.32(m, 10H) 883 δ = 8.81(d, 2H), 8.51(d,1H), 8.28-8.16(m, 4H), 8.06(d, 1H), 7.89-7.81(m, 7H), 7.70-7.32(m, 15H)885 δ = 8.81(d, 2H), 8.51(d, 1H), 8.33-8.23(m, 7H), 8.16(d, 1H), 8.06(d,1H), 7.89-7.81(m, 4H), 7.67(t, 3H), 7.52- 7.32(m, 10H) 893 δ = 9.30(d,2H), 9.15(s, 2H), 8.81(d, 2H), 8.52(d, 3H), 8.16(d, 1H), 8.06(d, 1H),7.89-7.81(m, 4H), 7.70- 7.66(m, 5H), 7.38(t, 1H), 7.32(t, 1H), 7.25(d,4H), 7.14(t, 2H) 895 δ = 8.81(d, 2H), 8.28(d, 4H), 8.16(d, 2H), 8.05(s,1H), 7.88(d, 3H), 7.68-7.66(m, 4H), 7.51-7.32(m, 8H) 901 δ = 8.81(d,2H), 8.45-8.16(m, 12H), 8.05(s, 1H), 7.98(d, 1H), 7.89(d, 1H),7.68-7.32(m, 12H), 7.25(d, 2H) 904 δ = 8.81(d, 2H), 8.23(s, 1H), 8.16(d,2H), 8.05(s, 1H), 7.98-7.67(m, 15H), 7.57-7.32(m, 11H) 913 δ = 8.81(d,2H), 8.54(d, 1H), 8.45-8.16(m, 11H), 7.98(d, 3H), 7.89(d, 1H),7.58-7.41(m, 9H), 7.38- 7.25(m, 4H) 915 δ = 8.81(d, 2H), 8.54(d, 1H),8.30(d, 4H), 8.23(s, 1H), 8.16(d, 1H), 7.98(d, 2H), 7.89-7.85(m, 7H),7.67(t, 3H), 7.51-7.32(m, 12H) 920 δ = 8.81(d, 2H), 8.54(d, 1H), 8.16(d,1H), 7.98(d, 2H), 7.88(d, 3H), 7.77-7.66(m, 9H), 7.52-7.32(m, 10H) 921 δ= 9.15(s, 1H), 8.93(d, 2H), 8.84(d, 4H), 8.45(d, 1H), 8.30(d, 2H),8.21-7.98(m, 10H), 7.88-7.80(m, 5H), 7.66(t, 1H), 7.54-7.47(m, 5H),7.35(d, 2H) 924 δ = 8.84(d, 4H), 8.30(d, 2H), 8.10-7.89(m, 7H), 7.81(d,1H), 7.66(d, 1H), 7.54-7.32(m, 12H), 7.25(d, 4H) 925 δ = 8.72(s, 1H),8.45(d, 1H), 8.31(d, 4H), 8.21(d, 1H), 8.10-7.98(m, 5H), 7.81(d, 1H),7.64(t, 2H), 7.54- 7.41(m, 10H), 7.35(d, 2H), 7.25(d, 4H) 926 δ =8.78(s, 1H), 8.72(s, 1H), 8.54-8.45(m, 3H), 8.31(d, 4H), 8.15-7.98(m,5H), 7.81(d, 1H), 7.63-7.50(m, 7H), 7.35(d, 2H), 7.26(d, 1H), 7.00(t,1H) 928 δ = 8.72(s, 1H), 8.31(d, 4H), 8.10-8.03(m, 4H), 7.95- 7.89(m,3H), 7.80(d, 3H), 7.64(t, 2H), 7.54-7.32(m, 10H) 929 δ = 8.81(d, 2H),8.45(d, 1H), 8.30(d, 4H), 8.21(d, 1H), 8.10-7.98(m, 5H), 7.81(d, 1H),7.66(t, 1H), 7.54- 7.47(m, 8H), 7.35-7.28(d, 4H) 931 δ = 8.93(d, 2H),8.81(d, 2H), 8.32(d, 3H), 8.12-8.06(m, 5H), 7.93-7.66(m, 12H),7.54-7.32(m, 8H) 935 δ = 8.55(d, 1H), 8.46(d, 1H), 8.30-8.21(m, 5H),8.10- 8.04(m, 6H), 7.90(d, 2H), 7.81(d, 1H), 7.66-7.47(m, 9H),7.38-7.32(m, 4H) 937 δ = 8.84(d, 4H), 8.48(d, 1H), 8.30(d, 2H),8.16-7.98(m, 6H), 7.81(d, 2H), 7.67(d, 2H), 7.54-7.47(m, 5H), 7.35(d,2H) 938 δ = 8.84(d, 4H), 8.45(d, 1H), 8.30(d, 2H), 8.16-7.98(m, 7H),7.81(d, 1H), 7.67(d, 3H), 7.54-7.47(m, 5H), 7.35(d, 2H) 939 δ = 8.84(d,4H), 8.54(d, 1H), 8.30(d, 2H), 8.16-8.06(m, 4H), 7.99(d, 2H), 7.89(d,1H), 7.81(d, 2H), 7.67(td, 3H), 7.54-7.47(m, 3H), 7.38-7.32(m, 4H) 940 δ= 8.84(d, 4H), 8.51(d, 1H), 8.30(d, 2H), 8.16-8.06(m, 5H), 7.89(d, 1H),7.81(d, 2H), 7.67(td, 3H), 7.54- 7.47(m, 3H), 7.38-7.32(m, 4H) 942 δ =8.81(d, 4H), 8.54(d, 1H), 8.45(d, 1H), 8.30(d, 2H), 8.16-8.06(m, 4H),7.99(d, 3H), 7.88-7.81(m, 5H), 7.67(t, 2H), 7.54-7.47(m, 5H), 7.35(d,2H) 944 δ = 8.81(d, 4H), 8.30(d, 2H), 8.16-8.05(m, 6H), 7.89- 7.81(m,6H), 7.67(t, 4H), 7.54-7.47(m, 3H), 7.35(m, 4H)

TABLE 52 Compound FD-Mass Compound FD-Mass 1 m/z = 762.92 2 m/z = 708.83(C54H32N4S = 768.23) (C48H28N4OS = 708.20) 3 m/z = 845.02 4 m/z = 800.99(C60H36N4S = 844.27) (C54H32N4S2 = 800.21) 5 m/z = 784.92 6 m/z = 770.94(C54H32N4OS = 784.23) (C54H34N4S = 770.25) 7 m/z = 783.94 8 m/z = 783.94(C54H33N5S = 783.25) (C54H33N5S = 783.25) 9 m/z = 784.92 10 m/z = 784.92(C54H32N4OS = 784.23) (C54H32N4OS = 784.23) 11 m/z = 784.92 12 m/z =800.99 (C54H32N4OS = 784.23) (C54H32N4S2 = 800.21) 13 m/z = 800.99 14m/z = 784.92 (C54H32N4S2 = 800.21) (C54H32N4OS = 784.23) 15 m/z = 770.9416 m/z = 847.04 (C54H34N4S = 770.25) (C60H38N4S = 846.28) 17 m/z =768.92 18 m/z = 784.92 (C54H32N4S = 768.23) (C54H32N4OS = 784.23) 19 m/z= 800.99 20 m/z = 770.94 (C54H32N4S2 = 800.21) (C54H34N4S = 770.25) 21m/z = 800.99 22 m/z = 770.94 (C54H32N4S2 = 800.21) (C54H34N4S = 770.25)23 m/z = 770.94 24 m/z = 783.94 (C54H34N4S = 770.25) (C54H33N5S =783.25) 25 m/z = 783.94 26 m/z = 784.92 (C54H33N5S = 783.25) (C54H32N4OS= 784.23) 27 m/z = 784.92 28 m/z = 784.92 (C54H32N4OS = 784.23)(C54H32N4OS = 784.23) 29 m/z = 800.99 30 m/z = 800.99 (C54H32N4S2 =800.21) (C54H32N4S2 = 800.21) 31 m/z = 800.99 32 m/z = 847.04(C54H32N4S2 = 800.21) (C60H38N4S = 846.28) 33 m/z = 768.92 34 m/z =784.92 (C54H32N4S = 768.23) (C54H32N4OS = 784.23) 35 m/z = 800.99 36 m/z= 770.94 (C54H32N4S2 = 800.21) (C54H34N4S = 770.25) 37 m/z = 783.94 38m/z = 783.94 (C54H33N5S = 783.25) (C54H33N5S = 783.25) 39 m/z = 784.9240 m/z = 784.92 (C54H32N4OS = 784.23) (C54H32N4OS = 784.23) 41 m/z =800.99 42 m/z = 800.99 (C54H32N4S2 = 800.21) (C54H32N4S2 = 800.21) 43m/z = 784.92 44 m/z = 770.94 (C54H32N4OS = 784.23) (C54H34N4S = 770.25)45 m/z = 770.94 46 m/z = 768.92 (C54H34N4S = 770.25) (C54H32N4S =768.23) 47 m/z = 708.83 48 m/z = 724.89 (C48H28N4OS = 708.20)(C48H28N4S2 = 724.18) 49 m/z = 800.99 50 m/z = 770.94 (C54H32N4S2 =800.21) (C54H34N4S = 770.25) 51 m/z = 783.94 52 m/z = 783.94 (C54H33N5S= 783.25) (C54H33N5S = 783.25) 53 m/z = 784.92 54 m/z = 784.92(C54H32N4OS = 784.23) (C54H32N4OS = 784.23) 55 m/z = 800.99 56 m/z =800.99 (C54H32N4S2 = 800.21) (C54H32N4S2 = 800.21) 57 m/z = 784.92 58m/z = 847.04 (C54H32N4OS = 784.23) (C60H38N4S = 846.28) 59 m/z = 668.8160 m/z = 708.83 (C46H28N4S = 668.20) (C48H28N4OS = 708.20) 61 m/z =800.99 62 m/z = 770.94 (C54H32N4S2 = 800.21) (C54H34N4S = 770.25) 63 m/z= 800.99 64 m/z = 770.94 (C54H32N4S2 = 800.21) (C54H34N4S = 770.25) 65m/z = 783.94 66 m/z = 783.94 (C54H33N5S = 783.25) (C54H33N5S = 783.25)67 m/z = 784.92 68 m/z = 784.92 (C54H32N4OS = 784.23) (C54H32N4OS =784.23) 69 m/z = 800.99 70 m/z = 847.04 (C54H32N4S2 = 800.21) (C60H38N4S= 846.28) 71 m/z = 767.94 72 m/z = 783.94 (C55H33N3S = 767.24)(C55H33N3OS = 783.23) 73 m/z = 800.00 74 m/z = 769.95 (C55H33N3S2 =799.21) (C55H35N3S = 769.26) 75 m/z = 782.95 76 m/z = 782.95 (C55H34N4S= 782.25) (C55H34N4S = 782.25) 77 m/z = 783.94 78 m/z = 783.94(C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 79 m/z = 800.00 80 m/z =800.00 (C55H33N3S2 = 799.21) (C55H33N3S2 = 799.21) 81 m/z = 783.94 82m/z = 846.05 (C55H33N3OS = 783.23) (C61H39N3S = 845.29) 83 m/z = 767.9484 m/z = 783.94 (C55H33N3S = 767.24) (C55H33N3OS = 783.23) 85 m/z =723.90 86 m/z = 793.97 (C49H29N3S2 = 723.18) (C57H35N3S = 793.26) 87 m/z= 800.00 88 m/z = 769.95 (C55H33N3S2 = 799.21) (C55H35N3S = 769.26) 89m/z = 782.95 90 m/z = 782.95 (C55H34N4S = 782.25) (C55H34N4S = 782.25)91 m/z = 783.94 92 m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS =783.23) 93 m/z = 773.96 94 m/z = 800.00 (C53H31N3S2 = 773.20)(C55H33N3S2 = 799.21) 95 m/z = 783.94 96 m/z = 769.95 (C55H33N3OS =783.23) (C55H35N3S = 769.26) 97 m/z = 767.94 98 m/z = 783.94 (C55H33N3S= 767.24) (C55H33N3OS = 783.23) 99 m/z = 723.90 100 m/z = 769.95(C49H29N3S2 = 723.18) (C55H35N3S = 769.26) 101 m/z = 800.00 102 m/z =769.95 (C55H33N3S2 = 799.21) (C55H35N3S = 769.26) 103 m/z = 782.95 104m/z = 782.95 (C55H34N4S = 782.25) (C55H34N4S = 782.25) 105 m/z = 783.94106 m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 107 m/z =800.00 108 m/z = 800.00 (C55H33N3S2 = 799.21) (C55H33N3S2 = 799.21) 109m/z = 769.95 110 m/z = 769.95 (C55H35N3S = 769.26) (C55H35N3S = 769.26)111 m/z = 667.82 112 m/z = 783.94 (C47H29N3S = 667.21 (C55H33N3OS =783.23) 113 m/z = 723.90 114 m/z = 769.95 (C49H29N3S2 = 723.18)(C55H35N3S = 769.26) 115 m/z = 800.00 116 m/z = 769.95 (C55H33N3S2 =799.21) (C55H35N3S = 769.26) 117 m/z = 782.95 118 m/z = 782.95(C55H34N4S = 782.25) (C55H34N4S = 782.25) 119 m/z = 783.94 120 m/z =783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 121 m/z = 800.00 122m/z = 800.00 (C55H33N3S2 = 799.21) (C55H33N3S2 = 799.21) 123 m/z =769.95 124 m/z = 769.95 (C55H35N3S = 769.26) (C55H35N3S = 769.26) 125m/z = 767.94 126 m/z = 783.94 (C55H33N3S = 767.24) (C55H33N3OS = 783.23)127 m/z = 800.00 128 m/z = 800.00 (C55H33N3S2 = 799.21) (C55H33N3S2 =799.21) 129 m/z = 769.95 130 m/z = 782.95 (C55H35N3S = 769.26)(C55H34N4S = 782.25) 131 m/z = 782.95 132 m/z = 783.94 (C55H34N4S =782.25) (C55H33N3OS = 783.23) 133 m/z = 783.94 134 m/z = 800.00(C55H33N3OS = 783.23) (C55H33N3S2 = 799.21) 135 m/z = 800.00 136 m/z =783.94 (C55H33N3S2 = 799.21) (C55H33N3OS = 783.23) 137 m/z = 846.05 138m/z = 767.94 (C61H39N3S = 845.29) (C55H33N3S = 767.24) 139 m/z = 783.94140 m/z = 800.00 (C55H33N3OS = 783.23) (C55H33N3S2 = 799.21) 141 m/z =844.03 142 m/z = 800.00 (C61H37N3S = 843.27) (C55H33N3S2 = 799.21) 143m/z = 782.95 144 m/z = 782.95 (C55H34N4S = 782.25) (C55H34N4S = 782.25)145 m/z = 783.94 146 m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS =783.23) 147 m/z = 800.00 148 m/z = 800.00 (C55H33N3S2 = 799.21)(C55H33N3S2 = 799.21) 149 m/z = 783.94 150 m/z = 846.05 (C55H33N3OS =783.23) (C61H39N3S = 845.29) 151 m/z = 767.94 152 m/z = 783.94(C55H33N3S = 767.24) (C55H33N3OS = 783.23) 153 m/z = 723.90 154 m/z =769.95 (C49H29N3S2 = 723.18) (C55H35N3S = 769.26) 155 m/z = 769.95 156m/z = 769.95 (C55H35N3S = 769.26) (C55H35N3S = 769.26) 157 m/z = 782.95158 m/z = 783.94 (C55H34N4S = 782.25) (C55H33N3OS = 783.23) 159 m/z =783.94 160 m/z = 800.00 (C55H33N3OS = 783.23) (C55H33N3S2 = 799.21) 161m/z = 800.00 162 m/z = 783.94 (C55H33N3S2 = 799.21) (C55H33N3OS =783.23) 163 m/z = 769.95 164 m/z = 846.05 (C55H35N3S = 769.26)(C61H39N3S = 845.29) 165 m/z = 667.82 166 m/z = 783.94 (C47H29N3S =667.21 (C55H33N3OS = 783.23) 167 m/z = 723.90 168 m/z = 769.95(C49H29N3S2 = 723.18) (C55H35N3S = 769.26) 169 m/z = 769.95 170 m/z =782.95 (C55H35N3S = 769.26) (C55H34N4S = 782.25) 171 m/z = 783.94 172m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 173 m/z =783.94 174 m/z = 800.00 (C55H33N3OS = 783.23) (C55H33N3S2 = 799.21) 175m/z = 800.00 176 m/z = 783.94 (C55H33N3S2 = 799.21) (C55H33N3OS =783.23) 177 m/z = 769.95 178 m/z = 846.05 (C55H35N3S = 769.26)(C61H39N3S = 845.29) 179 m/z = 784.92 180 m/z = 770.94 (C54H32N4OS =784.23) (C54H34N4S = 770.25) 181 m/z = 794.96 182 m/z = 744.90(C56H34N4S = 794.25) (C52H32N4S = 744.23) 183 m/z = 784.92 184 m/z =770.94 (C54H32N4OS = 784.23) (C54H34N4S = 770.25) 185 m/z = 744.90 186m/z = 800.99 (C52H32N4S = 744.23) (C54H32N4S2 = 800.21) 187 m/z = 694.84188 m/z = 800.99 (C48H30N4S = 694.22) (C54H32N4S2 = 800.21) 189 m/z =794.96 190 m/z = 744.90 (C56H34N4S = 794.25) (C52H32N4S = 744.23) 191m/z = 784.92 192 m/z = 770.94 (C54H32N4OS = 784.23) (C54H34N4S = 770.25)193 m/z = 694.84 194 m/z = 800.99 (C48H30N4S = 694.22) (C54H32N4S2 =800.21) 195 m/z = 677.75 196 m/z = 739.86 (C45H28NO2PS = 677.16)(C51H34NOPS = 739.21) 197 m/z = 763.88 198 m/z = 769.91 (C53H34NOPS =763.21) (C51H32NOPS2 = 769.17) 199 m/z = 753.84 200 m/z = 739.86(C51H32NO2PS = 753.19) (C51H34NOPS = 739.21) 201 m/z = 713.82 202 m/z =769.91 (C49H32NOPS = 713.19) (C51H32NOPS2 = 769.17) 203 m/z = 663.76 204m/z = 769.91 (C45H30NOPS = 663.18) (C51H32NOPS2 = 769.17) 205 m/z =763.88 206 m/z = 713.82 (C53H34NOPS = 763.21) (C49H32NOPS = 713.19) 207m/z = 753.84 208 m/z = 739.86 (C51H32NO2PS = 753.19) (C51H34NOPS =739.21) 209 m/z = 663.76 210 m/z = 769.91 (C45H30NOPS = 663.18)(C51H32NOPS2 = 769.17) 211 m/z = 618.75 212 m/z = 783.94 (C42H26N4S =618.19) (C54H33N5S = 783.25) 213 m/z = 784.92 214 m/z = 770.94(C54H32N4OS = 784.23) (C54H34N4S = 770.25) 215 m/z = 770.94 216 m/z =783.94 (C54H34N4S = 770.25) (C54H33N5S = 783.25) 217 m/z = 800.99 218m/z = 770.94 (C54H32N4S2 = 800.21) (C54H34N4S = 770.25) 219 m/z = 618.75220 m/z = 783.94 (C42H26N4S = 618.19) (C55H33N3OS = 783.23) 221 m/z =784.92 222 m/z = 770.94 (C54H32N4OS = 784.23) (C54H34N4S = 770.25) 223m/z = 618.75 224 m/z = 783.94 (C42H26N4S = 618.19) (C54H33N5S = 783.25)225 m/z = 784.92 226 m/z = 770.94 (C54H32N4OS = 784.23) (C54H34N4S =770.25) 227 m/z = 769.95 228 m/z = 782.95 (C55H35N3S = 769.26)(C55H34N4S = 782.25) 229 m/z = 783.94 230 m/z = 769.95 (C55H33N3OS =783.23) (C55H35N3S = 769.26) 231 m/z = 617.76 232 m/z = 782.95(C43H27N3S = 617.19) (C55H34N4S = 782.25) 233 m/z = 800.00 234 m/z =769.95 (C55H33N3S2 = 799.21) (C55H35N3S = 769.26) 235 m/z = 769.95 236m/z = 782.95 (C55H35N3S = 769.26) (C55H34N4S = 782.25) 237 m/z = 783.94238 m/z = 800.00 (C55H33N3OS = 783.23) (C55H33N3S2 = 799.21) 239 m/z =617.76 240 m/z = 782.95 (C43H27N3S = 617.19) (C55H34N4S = 782.25) 241m/z = 783.94 242 m/z = 769.95 (C55H33N3OS = 783.23) (C55H35N3S = 769.26)243 m/z = 769.95 244 m/z = 782.95 (C55H35N3S = 769.26) (C55H34N4S =782.25) 245 m/z = 800.00 246 m/z = 769.95 (C55H33N3S2 = 799.21)(C55H35N3S = 769.26) 247 m/z = 617.76 248 m/z = 782.95 (C43H27N3S =617.19) (C55H34N4S = 782.25) 249 m/z = 783.94 250 m/z = 769.95(C55H33N3OS = 783.23) (C55H35N3S = 769.26) 251 m/z = 769.95 252 m/z =782.95 (C55H35N3S = 769.26) (C55H34N4S = 782.25) 253 m/z = 800.00 254m/z = 769.95 (C55H33N3S2 = 799.21) (C55H35N3S = 769.26) 255 m/z = 617.76256 m/z = 782.95 (C43H27N3S = 617.19) (C55H34N4S = 782.25) 257 m/z =800.00 258 m/z = 783.94 (C55H33N3S2 = 799.21) (C55H33N3OS = 783.23) 259m/z = 618.75 260 m/z = 618.75 (C42H26N4S = 618.19) (C42H26N4S = 618.19)261 m/z = 694.84 262 m/z = 618.75 (C48H30N4S = 694.22) (C42H26N4S =618.19) 263 m/z = 618.75 264 m/z = 694.84 (C42H26N4S = 618.19)(C48H30N4S = 694.22) 265 m/z = 618.75 266 m/z = 618.75 (C42H26N4S =618.19) (C42H26N4S = 618.19) 267 m/z = 694.84 268 m/z = 618.75(C48H30N4S = 694.22) (C42H26N4S = 618.19) 269 m/z = 618.75 270 m/z =694.84 (C42H26N4S = 618.19) (C48H30N4S = 694.22) 271 m/z = 587.67 272m/z = 663.76 (C39H26NOPS = 587.15) (C45H30NOPS = 663.18) 273 m/z =663.76 274 m/z = 587.67 (C45H30NOPS = 663.18) (C39H26NOPS = 587.15) 275m/z = 663.76 276 m/z = 663.76 (C45H30NOPS = 663.18) (C45H30NOPS =663.18) 277 m/z = 587.67 278 m/z = 663.76 (C39H26NOPS = 587.15)(C45H30NOPS = 663.18) 279 m/z = 663.76 280 m/z = 587.67 (C45H30NOPS =663.18) (C39H26NOPS = 587.15) 281 m/z = 663.76 282 m/z = 663.76(C45H30NOPS = 663.18) (C45H30NOPS = 663.18) 283 m/z = 668.81 284 m/z =834.00 (C46H28N4S = 668.20) (C58H35N5S = 833.26) 285 m/z = 834.98 286m/z = 821.00 (C58H34N4OS = 834.25) (C58H36N4S = 820.27) 287 m/z = 821.00288 m/z = 834.00 (C58H36N4S = 820.27) (C58H35N5S = 833.26) 289 m/z =851.05 290 m/z = 821.00 (C58H34N4S2 = 850.22) (C58H36N4S = 820.27) 291m/z = 668.81 292 m/z = 834.00 (C46H28N4S = 668.20) (C58H35N5S = 833.26)293 m/z = 834.98 294 m/z = 821.00 (C58H34N4OS = 834.25) (C58H36N4S =820.27) 295 m/z = 668.81 296 m/z = 834.00 (C46H28N4S = 668.20)(C58H35N5S = 833.26) 297 m/z = 834.98 298 m/z = 821.00 (C58H34N4OS =834.25) (C58H36N4S = 820.27) 299 m/z = 820.01 300 m/z = 833.01(C59H37N3S = 819.27) (C59H36N4S = 832.27) 301 m/z = 833.99 302 m/z =820.01 (C59H35N3OS = 833.25) (C59H37N3S = 819.27) 303 m/z = 833.01 304m/z = 833.01 (C59H36N4S = 832.27) (C59H36N4S = 832.27) 305 m/z = 850.06306 m/z = 820.01 (C59H35N3S2 = 849.23) (C59H37N3S = 819.27) 307 m/z =820.01 308 m/z = 833.01 (C59H37N3S = 819.27) (C59H36N4S = 832.27) 309m/z = 833.99 310 m/z = 850.06 (C59H35N3OS = 833.25) (C59H35N3S2 =849.23) 311 m/z = 667.82 312 m/z = 833.01 (C47H29N3S = 667.21)(C59H36N4S = 832.27) 313 m/z = 833.99 314 m/z = 820.01 (C59H35N3OS =833.25) (C59H37N3S = 819.27) 315 m/z = 820.01 316 m/z = 833.01(C59H37N3S = 819.27) (C59H36N4S = 832.27) 317 m/z = 850.06 318 m/z =820.01 (C59H35N3S2 = 849.23) (C59H37N3S = 819.27) 319 m/z = 667.82 320m/z = 833.01 (C47H29N3S = 667.21) (C59H36N4S = 832.27) 321 m/z = 833.99322 m/z = 820.01 (C59H35N3OS = 833.25) (C59H37N3S = 819.27) 323 m/z =820.01 324 m/z = 833.01 (C59H37N3S = 819.27) (C59H36N4S = 832.27) 325m/z = 850.06 326 m/z = 820.01 (C59H35N3S2 = 849.23) (C59H37N3S = 819.27)327 m/z = 667.82 328 m/z = 833.01 (C47H29N3S = 667.21) (C59H36N4S =832.27) 329 m/z = 850.06 330 m/z = 833.99 (C59H35N3S2 = 849.23)(C59H35N3OS = 833.25) 331 m/z = 668.81 332 m/z = 668.81 (C46H28N4S =668.20) (C46H28N4S = 668.20) 333 m/z = 668.81 334 m/z = 668.81(C46H28N4S = 668.20) (C46H28N4S = 668.20) 335 m/z = 668.81 336 m/z =744.90 (C46H28N4S = 668.20) (C52H32N4S = 744.23) 337 m/z = 668.81 338m/z = 668.81 (C46H28N4S = 668.20) (C46H28N4S = 668.20) 339 m/z = 744.90340 m/z = 668.81 (C52H32N4S = 744.23) (C46H28N4S = 668.20) 341 m/z =668.81 342 m/z = 744.90 (C46H28N4S = 668.20) (C52H32N4S = 744.23) 343m/z = 637.73 344 m/z = 713.82 (C43H28NOPS = 637.16) (C49H32NOPS =713.19) 345 m/z = 713.82 346 m/z = 637.73 (C49H32NOPS = 713.19)(C43H28NOPS = 637.16) 347 m/z = 713.82 348 m/z = 713.82 (C49H32NOPS =713.19) (C49H32NOPS = 713.19) 349 m/z = 637.73 350 m/z = 713.82(C43H28NOPS = 637.16) (C49H32NOPS = 713.19) 351 m/z = 713.82 352 m/z =637.73 (C49H32NOPS = 713.19) (C43H28NOPS = 637.16) 353 m/z = 713.82 354m/z = 713.82 (C49H32NOPS = 713.19) (C49H32NOPS = 713.19) 355 m/z =718.87 356 m/z = 794.96 (C50H30N4S = 718.22) (C56H34N4S = 794.25) 357m/z = 794.96 358 m/z = 794.96 (C56H34N4S = 794.25) (C56H34N4S = 794.25)359 m/z = 718.87 360 m/z = 794.96 (C50H30N4S = 718.22) (C56H34N4S =794.25) 361 m/z = 718.87 362 m/z = 794.96 (C50H30N4S = 718.22)(C56H34N4S = 794.25) 363 m/z = 717.88 364 m/z = 793.97 (C51H31N3S =717.22) (C57H35N3S = 793.26) 365 m/z = 793.97 366 m/z = 793.97(C57H35N3S = 793.26) (C57H35N3S = 793.26) 367 m/z = 717.88 368 m/z =793.97 (C51H31N3S = 717.22) (C57H35N3S = 793.26) 369 m/z = 717.88 370m/z = 793.97 (C51H31N3S = 717.22) (C57H35N3S = 793.26) 371 m/z = 717.88372 m/z = 793.97 (C51H31N3S = 717.22) (C57H35N3S = 793.26) 373 m/z =793.97 374 m/z = 793.97 (C57H35N3S = 793.26) (C57H35N3S = 793.26) 375m/z = 717.88 376 m/z = 793.97 (C51H31N3S = 717.22) (C57H35N3S = 793.26)377 m/z = 717.88 378 m/z = 793.97 (C51H31N3S = 717.22) (C57H35N3S =793.26) 379 m/z = 718.87 380 m/z = 794.96 (C50H30N4S = 718.22)(C56H34N4S = 794.25) 381 m/z = 718.87 382 m/z = 794.96 (C50H30N4S =718.22) (C56H34N4S = 794.25) 383 m/z = 718.87 384 m/z = 794.96(C50H30N4S = 718.22) (C56H34N4S = 794.25) 385 m/z = 718.87 386 m/z =794.96 (C50H30N4S = 718.22) (C56H34N4S = 794.25) 387 m/z = 687.79 388m/z = 763.88 (C47H30NOPS = 687.18) (C53H34NOPS = 763.21) 389 m/z =687.79 390 m/z = 763.88 (C47H30NOPS = 687.18) (C53H34NOPS = 763.21) 391m/z = 687.79 392 m/z = 763.88 (C47H30NOPS = 687.18) (C53H34NOPS =763.21) 393 m/z = 687.79 394 m/z = 763.88 (C47H30NOPS = 687.18)(C53H34NOPS = 763.21) 395 m/z = 768.92 396 m/z = 845.02 (C54H32N4S =768.23) (C60H36N4S = 844.27) 397 m/z = 768.92 398 m/z = 845.02(C54H32N4S = 768.23) (C60H36N4S = 844.27) 399 m/z = 768.92 400 m/z =768.92 (C54H32N4S = 768.23) (C54H32N4S = 768.23) 401 m/z = 767.94 402m/z = 844.03 (C55H33N3S = 767.24) (C61H37N3S = 843.27) 403 m/z = 767.94404 m/z = 844.03 (C55H33N3S = 767.24) (C61H37N3S = 843.27) 405 m/z =767.94 406 m/z = 844.03 (C55H33N3S = 767.24) (C61H37N3S = 843.27) 407m/z = 767.94 408 m/z = 844.03 (C55H33N3S = 767.24) (C61H37N3S = 843.27)409 m/z = 767.94 410 m/z = 844.03 (C55H33N3S = 767.24) (C61H37N3S =843.27) 411 m/z = 767.94 412 m/z = 767.94 (C55H33N3S = 767.24)(C55H33N3S = 767.24) 413 m/z = 768.92 414 m/z = 768.92 (C54H32N4S =768.23) (C54H32N4S = 768.23) 415 m/z = 768.92 416 m/z = 768.92(C54H32N4S = 768.23) (C54H32N4S = 768.23) 417 m/z = 737.84 418 m/z =737.84 (C51H32NOPS = 737.19) (C51H32NOPS = 737.19) 419 m/z = 737.84 420m/z = 737.84 (C51H32NOPS = 737.19) (C51H32NOPS = 737.19) 421 m/z =592.71 422 m/z = 757.90 (C40H24N4S = 592.17) (C52H31N5S = 757.23) 423m/z = 758.89 424 m/z = 744.90 (C52H30N4OS = 758.21) (C52H32N4S = 744.23)425 m/z = 667.82 426 m/z = 756.91 (C47H29N3S = 667.21) (C53H32N4S =756.23) 427 m/z = 773.96 428 m/z = 820.01 (C53H31N3S2 = 773.20)(C59H37N3S = 819.27) 429 m/z = 743.91 430 m/z = 756.91 (C53H33N3S =743.24) (C53H32N4S = 756.23) 431 m/z = 757.90 432 m/z = 743.91(C53H31N3OS = 757.22) (C53H33N3S = 743.24) 433 m/z = 668.81 434 m/z =637.73 (C46H28N4S = 668.20) (C43H28NOPS = 637.16) 435 m/z = 592.71 436m/z = 757.90 (C40H24N4S = 592.17) (C52H31N5S = 757.23) 437 m/z = 758.89438 m/z = 744.90 (C52H30N4OS = 758.21) (C52H32N4S = 744.23) 439 m/z =667.82 440 m/z = 756.91 (C47H29N3S = 667.21) (C53H32N4S = 756.23) 441m/z = 773.96 442 m/z = 743.91 (C53H31N3S2 = 773.20) (C53H33N3S = 743.24)443 m/z = 756.91 444 m/z = 757.90 (C53H32N4S = 756.23) (C53H31N3OS =757.22) 445 m/z = 743.91 446 m/z = 668.81 (C53H33N3S = 743.24)(C46H28N4S = 668.20) 447 m/z = 637.73 448 m/z = 592.71 (C43H28NOPS =637.16) (C40H24N4S = 592.17) 449 m/z = 757.90 450 m/z = 758.89(C53H31N3OS = 757.22) (C52H30N4OS = 758.21) 451 m/z = 744.90 452 m/z =756.91 (C52H32N4S = 744.23) (C53H32N4S = 756.23) 453 m/z = 773.96 454m/z = 820.01 (C53H31N3S2 = 773.20) (C59H37N3S = 819.27) 455 m/z = 743.91456 m/z = 756.91 (C53H33N3S = 743.24) (C53H32N4S = 756.23) 457 m/z =757.90 458 m/z = 743.91 (C53H31N3OS = 757.22) (C53H33N3S = 743.24) 459m/z = 668.81 460 m/z = 637.73 (C46H28N4S = 668.20) (C43H28NOPS = 637.16)461 m/z = 752.86 462 m/z = 692.76 (C54H32N4O = 752.26) (C48H28N4O2 =692.22) 463 m/z = 828.95 464 m/z = 784.92 (C60H36N4O = 828.29)(C54H32N4OS = 784.23) 465 m/z = 768.86 466 m/z = 754.87 (C54H32N4O2 =768.25) (C54H34N4O = 754.27) 467 m/z = 767.87 468 m/z = 767.87(C54H33N5O = 767.27) (C54H33N5O = 767.27) 469 m/z = 768.86 470 m/z =768.86 (C54H32N4O2 = 768.25) (C54H32N4O2 = 768.25) 471 m/z = 768.86 472m/z = 784.92 (C54H32N4O2 = 768.25) (C54H32N4OS = 784.23) 473 m/z =784.92 474 m/z = 754.87 (C54H32N4OS = 784.23) (C54H34N4O = 754.27) 475m/z = 754.87 476 m/z = 830.97 (C54H34N4O = 754.27) (C60H38N4O = 830.30)477 m/z = 752.86 478 m/z = 768.86 (C54H32N4O = 752.26) (C54H32N4O2 =768.25) 479 m/z = 784.92 480 m/z = 754.87 (C54H32N4OS = 784.23)(C54H34N4O = 754.27) 481 m/z = 784.92 482 m/z = 754.87 (C54H32N4OS =784.23) (C54H34N4O = 754.27) 483 m/z = 754.87 484 m/z = 767.87(C54H34N4O = 754.27) (C54H33N5O = 767.27) 485 m/z = 767.87 486 m/z =768.86 (C54H33N5O = 767.27) (C54H32N4O2 = 768.25) 487 m/z = 768.86 488m/z = 768.86 (C54H32N4O2 = 768.25) (C54H32N4O2 = 768.25) 489 m/z =784.92 490 m/z = 784.92 (C54H32N4OS = 784.23) (C54H32N4OS = 784.23) 491m/z = 784.92 492 m/z = 830.97 (C54H32N4OS = 784.23) (C60H38N4O = 830.30)493 m/z = 752.86 494 m/z = 768.86 (C54H32N4O = 752.26) (C54H32N4O2 =768.25) 495 m/z = 784.92 496 m/z = 754.87 (C54H32N4OS = 784.23)(C54H34N4O = 754.27) 497 m/z = 767.87 498 m/z = 767.87 (C54H33N5O =767.27) (C54H33N5O = 767.27) 499 m/z = 768.86 500 m/z = 768.86(C54H32N4O2 = 768.25) (C54H32N4O2 = 768.25) 501 m/z = 784.92 502 m/z =784.92 (C54H32N4OS = 784.23) (C54H32N4OS = 784.23) 503 m/z = 768.86 504m/z = 754.87 (C54H32N4O2 = 768.25) (C54H34N4O = 754.27) 505 m/z = 754.87506 m/z = 752.86 (C54H34N4O = 754.27) (C54H32N4O = 752.26) 507 m/z =692.76 508 m/z = 708.83 (C48H28N4O2 = 692.22) (C48H28N4OS = 708.20) 509m/z = 784.92 510 m/z = 754.87 (C54H32N4OS = 784.23) (C54H34N4O = 754.27)511 m/z = 767.87 512 m/z = 767.87 (C54H33N5O = 767.27) (C54H33N5O =767.27) 513 m/z = 768.86 514 m/z = 768.86 (C54H32N4O2 = 768.25)(C54H32N4O2 = 768.25) 515 m/z = 784.92 516 m/z = 784.92 (C54H32N4OS =784.23) (C54H32N4OS = 784.23) 517 m/z = 768.86 518 m/z = 830.97(C54H32N4O2 = 768.25) (C60H38N4O = 830.30) 519 m/z = 652.74 520 m/z =692.76 (C46H28N4O = 652.23) (C48H28N4O2 = 692.22) 521 m/z = 784.92 522m/z = 754.87 (C54H32N4OS = 784.23) (C54H34N4O = 754.27) 523 m/z = 784.92524 m/z = 754.87 (C54H32N4OS = 784.23) (C54H34N4O = 754.27) 525 m/z =767.87 526 m/z = 767.87 (C54H33N5O = 767.27) (C54H33N5O = 767.27) 527m/z = 768.86 528 m/z = 768.86 (C54H32N4O2 = 768.25) (C54H32N4O2 =768.25) 529 m/z = 784.92 530 m/z = 830.97 (C54H32N4OS = 784.23)(C60H38N4O = 830.30) 531 m/z = 751.87 532 m/z = 767.87 (C55H33N3O =751.26) (C55H33N3O2 = 767.26) 533 m/z = 783.94 534 m/z = 753.89(C55H33N3OS = 783.23) (C55H35N3O = 753.28) 535 m/z = 766.88 536 m/z =766.88 (C55H34N4O = 766.27) (C55H34N4O = 766.27) 537 m/z = 767.87 538m/z = 767.87 (C55H33N3O2 = 767.26) (C55H33N3O2 = 767.26) 539 m/z =783.94 540 m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 541m/z = 767.87 542 m/z = 829.98 (C55H33N3O2 = 767.26) (C61H39N3O = 829.31)543 m/z = 751.87 544 m/z = 767.87 (C55H33N3O = 751.26) (C55H33N3O2 =767.26) 545 m/z = 707.84 546 m/z = 777.91 (C49H29N3OS = 707.20)(C57H35N3O = 777.28) 547 m/z = 783.94 548 m/z = 753.89 (C55H33N3OS =783.23) (C55H35N3O = 753.28) 549 m/z = 766.88 550 m/z = 766.88(C55H34N4O = 766.27) (C55H34N4O = 766.27) 551 m/z = 767.87 552 m/z =767.87 (C55H33N3O2 = 767.26) (C55H33N3O2 = 767.26) 553 m/z = 757.90 554m/z = 783.94 (C53H31N3OS = 757.22) (C55H33N3OS = 783.23) 555 m/z =767.87 556 m/z = 753.89 (C55H33N3O2 = 767.26) (C55H35N3O = 753.28) 557m/z = 751.87 558 m/z = 767.87 (C55H33N3O = 751.26) (C55H33N3O2 = 767.26)559 m/z = 707.84 560 m/z = 753.89 (C49H29N3OS = 707.20) (C55H35N3O =753.28) 561 m/z = 783.94 562 m/z = 753.89 (C55H33N3OS = 783.23)(C55H35N3O = 753.28) 563 m/z = 766.88 564 m/z = 766.88 (C55H34N4O =766.27) (C55H34N4O = 766.27) 565 m/z = 767.87 566 m/z = 767.87(C55H33N3O2 = 767.26) (C55H33N3O2 = 767.26) 567 m/z = 783.94 568 m/z =783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 569 m/z = 753.89 570m/z = 753.89 (C55H35N3O = 753.28) (C55H35N3O = 753.28) 571 m/z = 651.75572 m/z = 767.87 (C47H29N3O = 651.23) (C55H33N3O2 = 767.26) 573 m/z =707.84 574 m/z = 753.89 (C49H29N3OS = 707.20) (C55H35N3O = 753.28) 575m/z = 783.94 576 m/z = 753.89 (C55H33N3OS = 783.23) (C55H35N3O = 753.28)577 m/z = 766.88 578 m/z = 766.88 (C55H34N4O = 766.27) (C55H34N4O =766.27) 579 m/z = 767.87 580 m/z = 767.87 (C55H33N3O2 = 767.26)(C55H33N3O2 = 767.26) 581 m/z = 783.94 582 m/z = 783.94 (C55H33N3OS =783.23) (C55H33N3OS = 783.23) 583 m/z = 753.89 584 m/z = 753.89(C55H35N3O = 753.28) (C55H35N3O = 753.28) 585 m/z = 751.87 586 m/z =767.87 (C55H33N3O = 751.26) (C55H33N3O2 = 767.26) 587 m/z = 783.94 588m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 589 m/z =753.89 590 m/z = 766.88 (C55H35N3O = 753.28) (C55H34N4O = 766.27) 591m/z = 766.88 592 m/z = 767.87 (C55H34N4O = 766.27) (C55H33N3O2 = 767.26)593 m/z = 767.87 594 m/z = 783.94 (C55H33N3O2 = 767.26) (C55H33N3OS =783.23) 595 m/z = 783.94 596 m/z = 767.87 (C55H33N3OS = 783.23)(C55H33N3O2 = 767.26) 597 m/z = 829.98 598 m/z = 751.87 (C61H39N3O =829.31) (C55H33N3O = 751.26) 599 m/z = 767.87 600 m/z = 783.94(C55H33N3O2 = 767.26) (C55H33N3OS = 783.23) 601 m/z = 827.97 602 m/z =783.94 (C61H37N3O = 827.29) (C55H33N3OS = 783.23) 603 m/z = 766.88 604m/z = 766.88 (C55H34N4O = 766.27) (C55H34N4O = 766.27) 605 m/z = 767.87606 m/z = 767.87 (C55H33N3O2 = 767.26) (C55H33N3O2 = 767.26) 607 m/z =783.94 608 m/z = 783.94 (C55H33N3OS = 783.23) (C55H33N3OS = 783.23) 609m/z = 767.87 610 m/z = 829.98 (C55H33N3O2 = 767.26) (C61H39N3O = 829.31)611 m/z = 751.87 612 m/z = 767.87 (C55H33N3O = 751.26) (C55H33N3O2 =767.26) 613 m/z = 707.84 614 m/z = 753.89 (C49H29N3OS = 707.20)(C55H35N3O = 753.28) 615 m/z = 753.89 616 m/z = 766.88 (C55H35N3O =753.28) (C55H34N4O = 766.27) 617 m/z = 766.88 618 m/z = 767.87(C55H34N4O = 766.27) (C55H33N3O2 = 767.26) 619 m/z = 767.87 620 m/z =783.94 (C55H33N3O2 = 767.26) (C55H33N3OS = 783.23) 621 m/z = 783.94 622m/z = 767.87 (C55H33N3OS = 783.23) (C55H33N3O2 = 767.26) 623 m/z =753.89 624 m/z = 829.98 (C55H35N3O = 753.28) (C61H39N3O = 829.31) 625m/z = 651.75 626 m/z = 767.87 (C47H29N3O = 651.23) (C55H33N3O2 = 767.26)627 m/z = 707.84 628 m/z = 753.89 (C49H29N3OS = 707.20) (C55H35N3O =753.28) 629 m/z = 753.89 630 m/z = 766.88 (C55H35N3O = 753.28)(C55H34N4O = 766.27) 631 m/z = 766.88 632 m/z = 767.87 (C55H34N4O =766.27) (C55H33N3O2 = 767.26) 633 m/z = 767.87 634 m/z = 783.94(C55H33N3O2 = 767.26) (C55H33N3OS = 783.23) 635 m/z = 783.94 636 m/z =767.87 (C55H33N3OS = 783.23) (C55H33N3O2 = 767.26) 637 m/z = 753.89 638m/z = 829.98 (C55H35N3O = 753.28) (C61H39N3O = 829.31) 639 m/z = 768.86640 m/z = 754.87 (C54H32N4O2 = 768.25) (C54H34N4O = 754.27) 641 m/z =778.90 642 m/z = 728.84 (C56H34N4O = 778.27) (C52H32N4O = 728.26) 643m/z = 768.86 644 m/z = 754.87 (C54H32N4O2 = 768.25) (C54H34N4O = 754.27)645 m/z = 728.84 646 m/z = 784.92 (C52H32N4O = 728.26) (C54H32N4OS =784.23) 647 m/z = 678.78 648 m/z = 784.92 (C48H30N4O = 678.24)(C54H32N4OS = 784.23) 649 m/z = 778.90 650 m/z = 728.84 (C56H34N4O =778.27) (C52H32N4O = 728.26) 651 m/z = 768.86 652 m/z = 754.87(C54H32N4O2 = 768.25) (C54H34N4O = 754.27) 653 m/z = 678.78 654 m/z =784.92 (C48H30N4O = 678.24) (C54H32N4OS = 784.23) 655 m/z = 661.68 656m/z = 723.79 (C45H28NO3P = 661.18) (C51H34NO2P = 723.23) 657 m/z =747.82 658 m/z = 753.84 (C53H34NO2P = 747.23) (C51H32NO2PS = 753.19) 659m/z = 737.78 660 m/z = 723.79 (C51H32NO3P = 737.21) (C51H34NO2P =723.23) 661 m/z = 697.76 662 m/z = 753.84 (C49H32NO2P = 697.22)(C51H32NO2PS = 753.19) 663 m/z = 647.70 664 m/z = 753.84 (C45H30NO2P =647.20 (C51H32NO2PS = 753.19) 665 m/z = 747.82 666 m/z = 697.76(C53H34NO2P = 747.23) (C49H32NO2P = 697.22) 667 m/z = 737.78 668 m/z =723.79 (C51H32NO3P = 737.21) (C51H34NO2P = 723.23) 669 m/z = 647.70 670m/z = 753.84 (C45H30NO2P = 647.20 (C51H32NO2PS = 753.19) 671 m/z =602.68 672 m/z = 767.87 (C42H26N4O = 602.21) (C54H33N5O = 767.27) 673m/z = 768.86 674 m/z = 754.87 (C54H32N4O2 = 768.25) (C54H34N4O = 754.27)675 m/z = 754.87 676 m/z = 767.87 (C54H34N4O = 754.27) (C54H33N5O =767.27) 677 m/z = 784.92 678 m/z = 754.87 (C54H32N4OS = 784.23)(C54H34N4O = 754.27) 679 m/z = 602.68 680 m/z = 767.87 (C42H26N4O =602.21) (C54H33N5O = 767.27) 681 m/z = 768.86 682 m/z = 754.87(C54H32N4O2 = 768.25) (C54H34N4O = 754.27) 683 m/z = 602.68 684 m/z =767.87 (C42H26N4O = 602.21) (C54H33N5O = 767.27) 685 m/z = 768.86 686m/z = 754.87 (C54H32N4O2 = 768.25) (C54H34N4O = 754.27) 687 m/z = 753.89688 m/z = 766.88 (C55H35N3O = 753.28) (C55H34N4O = 766.27) 689 m/z =767.87 690 m/z = 753.89 (C55H33N3O2 = 767.26) (C55H35N3O = 753.28) 691m/z = 601.69 692 m/z = 766.88 (C43H27N3O = 601.22) (C55H34N4O = 766.27)693 m/z = 783.94 694 m/z = 753.89 (C55H33N3OS = 783.23) (C55H35N3O =753.28) 695 m/z = 753.89 696 m/z = 766.88 (C55H35N3O = 753.28)(C55H34N4O = 766.27) 697 m/z = 767.87 698 m/z = 783.94 (C55H33N3O2 =767.26) (C55H33N3OS = 783.23) 699 m/z = 601.69 700 m/z = 766.88(C43H27N3O = 601.22) (C55H34N4O = 766.27) 701 m/z = 767.87 702 m/z =753.89 (C55H33N3O2 = 767.26) (C55H35N3O = 753.28) 703 m/z = 753.89 704m/z = 766.88 (C55H35N3O = 753.28) (C55H34N4O = 766.27) 705 m/z = 783.94706 m/z = 753.89 (C55H33N3OS = 783.23) (C55H35N3O = 753.28) 707 m/z =601.69 708 m/z = 766.88 (C43H27N3O = 601.22) (C55H34N4O = 766.27) 709m/z = 767.87 710 m/z = 753.89 (C55H33N3O2 = 767.26) (C55H35N3O = 753.28)711 m/z = 753.89 712 m/z = 766.88 (C55H35N3O = 753.28) (C55H34N4O =766.27) 713 m/z = 783.94 714 m/z = 753.89 (C55H33N3OS = 783.23)(C55H35N3O = 753.28) 715 m/z = 601.69 716 m/z = 766.88 (C43H27N3O =601.22) (C55H34N4O = 766.27) 717 m/z = 783.94 718 m/z = 767.87(C55H33N3OS = 783.23) (C55H33N3O2 = 767.26) 719 m/z = 602.68 720 m/z =602.68 (C42H26N4O = 602.21) (C42H26N4O = 602.21) 721 m/z = 678.78 722m/z = 602.68 (C48H30N4O = 678.24) (C42H26N4O = 602.21) 723 m/z = 602.68724 m/z = 678.78 (C42H26N4O = 602.21) (C48H30N4O = 678.24) 725 m/z =602.68 726 m/z = 602.68 (C42H26N4O = 602.21) (C42H26N4O = 602.21) 727m/z = 678.78 728 m/z = 602.68 (C48H30N4O = 678.24) (C42H26N4O = 602.21)729 m/z = 602.68 730 m/z = 678.78 (C42H26N4O = 602.21) (C48H30N4O =678.24) 731 m/z = 571.60 732 m/z = 647.70 (C39H26NO2P = 571.17)(C45H30NO2P = 647.20) 733 m/z = 647.70 734 m/z = 571.60 (C45H30NO2P =647.20) (C39H26NO2P = 571.17) 735 m/z = 647.70 736 m/z = 647.70(C45H30NO2P = 647.20) (C45H30NO2P = 647.20) 737 m/z = 571.60 738 m/z =647.70 (C39H26NO2P = 571.17) (C45H30NO2P = 647.20) 739 m/z = 647.70 740m/z = 571.60 (C45H30NO2P = 647.20) (C39H26NO2P = 571.17) 741 m/z =647.70 742 m/z = 647.70 (C45H30NO2P = 647.20) (C45H30NO2P = 647.20) 743m/z = 652.74 744 m/z = 817.93 (C46H28N4O = 652.23) (C58H35N5O = 817.28)745 m/z = 818.92 746 m/z = 804.93 (C58H34N4O2 = 818.27) (C58H36N4O =804.29) 747 m/z = 804.93 748 m/z = 817.93 (C58H36N4O = 804.29)(C58H35N5O = 817.28) 749 m/z = 834.98 750 m/z = 804.93 (C58H34N4OS =834.25) (C58H36N4O = 804.29) 751 m/z = 652.74 752 m/z = 817.93(C46H28N4O = 652.23) (C58H35N5O = 817.28) 753 m/z = 818.92 754 m/z =804.93 (C58H35N5O = 818.27) (C58H36N4O = 804.29) 755 m/z = 652.74 756m/z = 817.93 (C46H28N4O = 652.23) (C58H35N5O = 817.28) 757 m/z = 818.92758 m/z = 804.93 (C58H35N5O = 818.27) (C58H36N4O = 804.29) 759 m/z =803.94 760 m/z = 816.94 (C59H37N3O = 803.29) (C59H36N4O = 816.29) 761m/z = 817.93 762 m/z = 803.94 (C58H35N5O = 817.28) (C59H37N3O = 803.29)763 m/z = 651.75 764 m/z = 816.94 (C47H29N3O = 651.23) (C59H36N4O =816.29) 765 m/z = 833.99 766 m/z = 803.94 (C59H35N3OS = 833.25)(C59H37N3O = 803.29) 767 m/z = 803.94 768 m/z = 816.94 (C59H37N3O =803.29) (C59H36N4O = 816.29) 769 m/z = 817.93 770 m/z = 833.99(C58H35N5O = 817.28) (C59H35N3OS = 833.25) 771 m/z = 651.75 772 m/z =816.94 (C47H29N3O = 651.23) (C59H36N4O = 816.29) 773 m/z = 817.93 774m/z = 803.94 (C58H35N5O = 817.28) (C59H37N3O = 803.29) 775 m/z = 803.94776 m/z = 816.94 (C59H37N3O = 803.29) (C59H36N4O = 816.29) 777 m/z =833.99 778 m/z = 803.94 (C59H35N3OS = 833.25) (C59H37N3O = 803.29) 779m/z = 651.75 780 m/z = 816.94 (C47H29N3O = 651.23) (C59H36N4O = 816.29)781 m/z = 817.93 782 m/z = 803.94 (C58H35N5O = 817.28) (C59H37N3O =803.29) 783 m/z = 803.94 784 m/z = 816.94 (C59H37N3O = 803.29)(C59H36N4O = 816.29) 785 m/z = 833.99 786 m/z = 803.94 (C59H35N3OS =833.25) (C59H37N3O = 803.29) 787 m/z = 651.75 788 m/z = 816.94(C47H29N3O = 651.23) (C59H36N4O = 816.29) 789 m/z = 833.99 790 m/z =817.93 (C59H35N3OS = 833.25) (C58H35N5O = 817.28) 791 m/z = 652.74 792m/z = 652.74 (C46H28N4O = 652.23) (C46H28N4O = 652.23) 793 m/z = 728.84794 m/z = 652.74 (C52H32N4O = 728.26) (C46H28N4O = 652.23) 795 m/z =652.74 796 m/z = 728.84 (C46H28N4O = 652.23) (C52H32N4O = 728.26) 797m/z = 652.74 798 m/z = 652.74 (C46H28N4O = 652.23) (C46H28N4O = 652.23)799 m/z = 728.84 800 m/z = 652.74 (C52H32N4O = 728.26) (C46H28N4O =652.23) 801 m/z = 652.74 802 m/z = 728.84 (C46H28N4O = 652.23)(C52H32N4O = 728.26) 803 m/z = 621.66 804 m/z = 697.76 (C43H28NO2P =621.19) (C49H32NO2P = 697.22) 805 m/z = 697.76 806 m/z = 621.66(C49H32NO2P = 697.22) (C43H28NO2P = 621.19) 807 m/z = 697.76 808 m/z =697.76 (C49H32NO2P = 697.22) (C49H32NO2P = 697.22) 809 m/z = 621.66 810m/z = 697.76 (C43H28NO2P = 621.19) (C49H32NO2P = 697.22) 811 m/z =697.76 812 m/z = 621.66 (C49H32NO2P = 697.22) (C43H28NO2P = 621.19) 813m/z = 697.76 814 m/z = 697.76 (C49H32NO2P = 697.22) (C49H32NO2P =697.22) 815 m/z = 702.80 816 m/z = 778.90 (C50H30N4O = 702.24)(C56H34N4O = 778.27) 817 m/z = 778.90 818 m/z = 778.90 (C56H34N4O =778.27) (C56H34N4O = 778.27) 819 m/z = 702.80 820 m/z = 778.90(C50H30N4O = 702.24) (C56H34N4O = 778.27) 821 m/z = 702.80 822 m/z =778.90 (C50H30N4O = 702.24) (C56H34N4O = 778.27) 823 m/z = 701.81 824m/z = 777.91 (C51H31N3O = 701.25) (C57H35N3O = 777.28) 825 m/z = 777.91826 m/z = 777.91 (C57H35N3O = 777.28) (C57H35N3O = 777.28) 827 m/z =701.81 828 m/z = 777.91 (C51H31N3O = 701.25) (C57H35N3O = 777.28) 829m/z = 701.81 830 m/z = 777.91 (C51H31N3O = 701.25) (C57H35N3O = 777.28)831 m/z = 701.81 832 m/z = 777.91 (C51H31N3O = 701.25) (C57H35N3O =777.28) 833 m/z = 777.91 834 m/z = 777.91 (C57H35N3O = 777.28)(C57H35N3O = 777.28) 835 m/z = 701.81 836 m/z = 777.91 (C51H31N3O =701.25) (C57H35N3O = 777.28) 837 m/z = 701.81 838 m/z = 777.91(C51H31N3O = 701.25) (C57H35N3O = 777.28) 839 m/z = 702.80 840 m/z =778.90 (C50H30N4O = 702.24) (C56H34N4O = 778.27) 841 m/z = 702.80 842m/z = 778.90 (C50H30N4O = 702.24) (C56H34N4O = 778.27) 843 m/z = 702.80844 m/z = 778.90 (C50H30N4O = 702.24) (C56H34N4O = 778.27) 845 m/z =702.80 846 m/z = 778.90 (C50H30N4O = 702.24) (C56H34N4O = 778.27) 847m/z = 671.72 848 m/z = 747.82 (C47H30NO2P = 671.20) (C53H34NO2P =747.23) 849 m/z = 671.72 850 m/z = 747.82 (C47H30NO2P = 671.20)(C53H34NO2P = 747.23) 851 m/z = 671.72 852 m/z = 747.82 (C47H30NO2P =671.20) (C53H34NO2P = 747.23) 853 m/z = 671.72 854 m/z = 747.82(C47H30NO2P = 671.20) (C53H34NO2P = 747.23) 855 m/z = 752.86 856 m/z =828.95 (C54H32N4O = 752.26) (C60H36N4O = 828.29) 857 m/z = 752.86 858m/z = 828.95 (C54H32N4O = 752.26) (C60H36N4O = 828.29) 859 m/z = 752.86860 m/z = 752.86 (C54H32N4O = 752.26) (C54H32N4O = 752.26) 861 m/z =751.87 862 m/z = 827.97 (C55H33N3O = 751.26) (C61H37N3O = 827.29) 863m/z = 751.87 864 m/z = 827.97 (C55H33N3O = 751.26) (C61H37N3O = 827.29)865 m/z = 751.87 866 m/z = 751.87 (C55H33N3O = 751.26) (C55H33N3O =751.26) 867 m/z = 751.87 868 m/z = 827.97 (C55H33N3O = 751.26)(C61H37N3O = 827.29) 869 m/z = 751.87 870 m/z = 827.97 (C55H33N3O =751.26) (C61H37N3O = 827.29) 871 m/z = 751.87 872 m/z = 751.87(C55H33N3O = 751.26) (C55H33N3O = 751.26) 873 m/z = 752.86 874 m/z =752.86 (C54H32N4O = 752.26) (C54H32N4O = 752.26) 875 m/z = 752.86 876m/z = 752.86 (C54H32N4O = 752.26) (C54H32N4O = 752.26) 877 m/z = 721.78878 m/z = 721.78 (C51H32NO2P = 721.22) (C51H32NO2P = 721.22) 879 m/z =721.78 880 m/z = 721.78 (C51H32NO2P = 721.22) (C51H32NO2P = 721.22) 881m/z = 576.64 882 m/z = 741.84 (C40H24N4O = 576.20) (C52H31N5O = 741.25)883 m/z = 742.82 884 m/z = 728.84 (C52H30N4O2 = 742.24) (C52H32N4O =728.26) 885 m/z = 651.75 886 m/z = 740.85 (C47H29N3O = 651.23)(C53H32N4O = 740.26) 887 m/z = 757.90 888 m/z = 803.94 (C53H31N3OS =757.22) (C59H37N3O = 803.29) 889 m/z = 727.85 890 m/z = 740.85(C53H33N3O = 727.26) (C53H32N4O = 740.26) 891 m/z = 741.83 892 m/z =727.85 (C53H31N3O2 = 741.24) (C53H33N3O = 727.26) 893 m/z = 652.74 894m/z = 621.66 (C46H28N4O = 652.23) (C43H28NO2P = 621.19) 895 m/z = 576.64896 m/z = 741.84 (C40H24N4O = 576.20) (C52H31N5O = 741.25) 897 m/z =742.82 898 m/z = 728.84 (C52H30N4O2 = 742.24) (C52H32N4O = 728.26) 899m/z = 651.75 900 m/z = 740.85 (C47H29N3O = 651.23) (C53H32N4O = 740.26)901 m/z = 757.90 902 m/z = 727.85 (C53H31N3OS = 757.22) (C53H33N3O =727.26) 903 m/z = 740.85 904 m/z = 741.84 (C53H32N4O = 740.26)(C52H31N5O = 741.25) 905 m/z = 727.85 906 m/z = 652.74 (C53H33N3O =727.26) (C46H28N4O = 652.23) 907 m/z = 621.66 908 m/z = 576.64(C43H28NO2P = 621.19) (C40H24N4O = 576.20) 909 m/z = 741.84 910 m/z =742.82 (C52H31N5O = 741.25) (C52H30N4O2 = 742.24) 911 m/z = 728.84 912m/z = 740.85 (C52H32N4O = 728.26) (C53H32N4O = 740.26) 913 m/z = 757.90914 m/z = 803.94 (C53H31N3OS = 757.22) (C59H37N3O = 803.29) 915 m/z =727.85 916 m/z = 740.85 (C53H33N3O = 727.26) (C53H32N4O = 740.26) 917m/z = 741.83 918 m/z = 727.85 (C53H31N3O2 = 741.24) (C53H33N3O = 727.26)919 m/z = 652.74 920 m/z = 621.66 (C46H28N4O = 652.23) (C43H28NO2P =621.19) 921 m/z = 791.96 922 m/z = 641.78 (C57H33N3S = 791.24)(C45H27N3S = 641.19) 923 m/z = 725.83 924 m/z = 701.81 (C53H31N3O =725.25) (C51H31N3O = 701.25) 925 m/z = 717.88 926 m/z = 642.77(C51H31N3S = 717.22) (C44H26N4S = 642.19) 927 m/z = 676.76 928 m/z =625.72 (C48H28N4O = 676.23) (C45H27N3O = 625.22) 929 m/z = 641.78 930m/z = 691.84 (C45H2d7N3S = 641.19) (C49H29N3S = 691.21) 931 m/z = 676.76932 m/z = 775.89 (C48H28N4O = 676.23) (C57H33N3O = 775.26) 933 m/z =791.96 934 m/z = 741.90 (C57H33N3S = 791.24) (C53H31N3S = 741.22) 935m/z = 675.77 936 m/z = 625.72 (C49H29N3O = 675.23) (C45H27N3O = 625.22)937 m/z = 615.74 938 m/z = 615.74 (C43H25N3S = 615.18) (C43H25N3S =615.18) 939 m/z = 599.68 940 m/z = 599.68 (C43H25N3O = 599.20)(C43H25N3O = 599.20) 941 m/z = 691.84 942 m/z = 691.84 (C49H29N3S =691.21) (C49H29N3S = 691.21) 943 m/z = 675.77 944 m/z = 675.77(C49H29N3O = 675.23) (C49H29N3O = 675.23) 945 m/z = 691.84 946 m/z =691.84 (C49H29N3S = 691.21) (C49H29N3S = 691.21) 947 m/z = 675.77 948m/z = 675.77 (C49H29N3O = 675.23) (C49H29N3O = 675.23)

<Experimental Example 1>—Manufacture of Organic Light Emitting Device

1) Manufacture of Organic Light Emitting Device

A transparent ITO electrode thin film obtained from glass for an OLED(manufactured by Samsung-Corning Co., Ltd.) was ultrasonic cleaned usingtrichloroethylene, acetone, ethanol and distilled water consecutivelyfor 5 minutes each, stored in isopropanol, and used.

Next, an ITO substrate was installed in a substrate folder of a vacuumdepositor, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) wasintroduced to a cell in the vacuum depositor.

Subsequently, the chamber was evacuated until the degree of vacuumtherein reached 10⁻⁶ torr, and then 2-TNATA was evaporated by applying acurrent to the cell to deposit a hole injection layer having a thicknessof 600 Å on the ITO substrate.

To another cell of the vacuum depositor, the followingN,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB) was introduced,and evaporated by applying a current to the cell to deposit a holetransfer layer having a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as below wasdeposited thereon as a light emitting layer. Specifically, in one sidecell in the vacuum depositor, H1, a blue light emitting host material,was vacuum deposited to a thickness of 200 Å, and D1, a blue lightemitting dopant material, was vacuum deposited thereon by 5% withrespect to the host material.

Subsequently, one of compounds described in the following Table 53 wasdeposited to a thickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was employed to have a thicknessof 1,000 Å to manufacture an OLED. Meanwhile, all the organic compoundsrequired to manufacture the OLED were vacuum sublimation purified under10⁻⁶ torr to 10⁻⁸ torr by each material to be used in the OLEDmanufacture.

For the organic electroluminescent device manufactured as above,electroluminescent light emission (EL) properties were measured usingM7000 manufactured by McScience Inc., and with the measurement results,T₉₅ when standard luminance was 700 cd/m² was measured using a lifetimemeasurement system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the blue organicelectroluminescent device manufactured according to the presentdisclosure are as shown in the following Table 53.

TABLE 53 Light Driving Emission Com- Voltage Efficiency CIE Lifetimepound (V) (cd/A) (x, y) (T95) Example 1 1 4.42 6.93 (0.134, 0.099) 40Example 2 7 4.48 6.86 (0.134, 0.099) 41 Example 3 10 4.47 6.87 (0.134,0.100) 40 Example 4 14 4.51 7.05 (0.134, 0.099) 42 Example 5 17 4.676.64 (0.129, 0.100) 38 Example 6 25 4.82 6.55 (0.130, 0.099) 36 Example7 28 4.77 6.68 (0.132, 0.098) 36 Example 8 33 4.44 6.97 (0.134, 0.101)40 Example 9 51 4.61 6.89 (0.134, 0.103) 40 Example 10 56 4.88 6.72(0.128, 0.099) 36 Example 11 57 4.70 6.75 (0.127, 0.100) 37 Example 1259 5.35 6.30 (0.134, 0.102) 33 Example 13 68 5.28 6.28 (0.134, 0.102) 32Example 14 69 5.61 6.19 (0.130, 0.099) 28 Example 15 72 5.60 6.07(0.129, 0.100) 29 Example 16 75 5.55 6.10 (0.130, 0.101) 30 Example 1778 5.71 6.15 (0.129, 0.098) 28 Example 18 83 4.57 6.74 (0.128, 0.099) 36Example 19 89 4.60 6.69 (0.129, 0.102) 36 Example 20 91 4.49 6.96(0.134, 0.100) 40 Example 21 98 4.62 6.72 (0.133, 0.100) 37 Example 22100 4.55 6.85 (0.134, 0.101) 39 Example 23 103 4.80 6.69 (0.130, 0.100)38 Example 24 106 5.42 6.13 (0.134, 0.101) 29 Example 25 112 5.67 6.02(0.132, 0.103) 25 Example 26 117 5.58 6.15 (0.130, 0.099) 25 Example 27119 5.70 6.07 (0.129, 0.100) 28 Example 28 124 4.54 6.92 (0.134, 0.101)41 Example 29 125 4.30 6.81 (0.134, 0.101) 41 Example 30 130 4.50 6.98(0.134, 0.100) 40 Example 31 134 4.44 7.09 (0.134, 0.100) 39 Example 32138 4.61 7.01 (0.134, 0.099) 38 Example 33 143 4.60 6.87 (0.131, 0.100)37 Example 34 149 4.64 7.08 (0.134, 0.099) 40 Example 35 151 4.53 6.91(0.134, 0.101) 41 Example 36 156 4.97 6.59 (0.134, 0.100) 34 Example 37159 4.54 6.95 (0.134, 0.103) 42 Example 38 166 5.33 6.17 (0.134, 0.102)29 Example 39 171 5.63 6.11 (0.131, 0.098) 28 Example 40 174 5.58 6.23(0.129, 0.101) 30 Example 41 178 5.61 6.20 (0.134, 0.102) 31 Example 42179 5.66 6.04 (0.131, 0.102) 30 Example 43 182 5.65 6.08 (0.134, 0.101)28 Example 44 186 5.35 6.32 (0.134, 0.102) 30 Example 45 190 5.43 6.25(0.134, 0.101) 29 Example 46 197 5.40 6.49 (0.134, 0.101) 31 Example 47199 5.59 6.14 (0.131, 0.101) 28 Example 48 203 5.60 6.22 (0.129, 0.100)29 Example 49 207 5.48 6.18 (0.129, 0.099) 28 Example 50 212 5.59 6.07(0.128, 0.102) 30 Example 51 217 4.74 5.89 (0.134, 0.100) 37 Example 52219 4.70 6.01 (0.134, 0.101) 36 Example 53 223 5.40 6.31 (0.134, 0.102)31 Example 54 228 5.71 6.19 (0.131, 0.100) 27 Example 55 231 5.63 6.06(0.128, 0.102) 27 Example 56 233 5.49 6.14 (0.130, 0.101) 29 Example 57236 4.73 6.78 (0.130, 0.100) 35 Example 58 243 4.67 6.65 (0.129, 0.098)36 Example 59 252 4.69 6.92 (0.130, 0.101) 35 Example 60 253 4.52 6.75(0.129, 0.097) 37 Example 61 256 5.32 6.22 (0.134, 0.102) 32 Example 62259 5.36 6.30 (0.134, 0.100) 34 Example 63 263 4.72 6.98 (0.134, 0.100)51 Example 64 265 4.80 6.89 (0.134, 0.102) 58 Example 65 272 4.76 6.95(0.134, 0.102) 50 Example 66 278 4.68 6.93 (0.134, 0.100) 50 Example 67283 4.88 6.84 (0.134, 0.102) 57 Example 68 288 4.77 6.90 (0.134, 0.102)51 Example 69 293 4.98 6.05 (0.134, 0.101) 34 Example 70 295 5.11 6.12(0.134, 0.102) 48 Example 71 305 4.96 6.10 (0.134, 0.100) 36 Example 72308 5.30 6.20 (0.134, 0.101) 40 Example 73 319 5.22 6.03 (0.134, 0.101)43 Example 74 324 4.82 6.84 (0.134, 0.101) 52 Example 75 328 4.84 6.97(0.134, 0.102) 51 Example 76 334 4.90 6.81 (0.134, 0.101) 56 Example 77347 4.88 6.82 (0.134, 0.102) 57 Example 78 352 4.74 6.75 (0.134, 0.101)51 Example 79 358 4.81 6.82 (0.134, 0.102) 53 Example 80 367 5.26 6.44(0.134, 0.102) 32 Example 81 373 5.21 6.38 (0.134, 0.101) 41 Example 82379 5.16 6.20 (0.134, 0.101) 38 Example 83 382 5.15 6.42 (0.134, 0.102)39 Example 84 389 5.31 6.30 (0.134, 0.103) 37 Example 85 393 5.33 6.22(0.134, 0.102) 40 Example 86 397 5.32 5.95 (0.134, 0.101) 41 Example 87406 4.82 6.35 (0.134, 0.100) 50 Example 88 415 4.84 6.60 (0.134, 0.100)49 Example 89 419 4.94 6.68 (0.134, 0.101) 52 Example 90 423 4.96 6.70(0.134, 0.101) 47 Example 91 425 4.91 6.69 (0.134, 0.102) 51 Example 92433 4.90 6.71 (0.134, 0.102) 50 Example 93 435 5.32 6.22 (0.134, 0.102)32 Example 94 441 5.36 6.30 (0.134, 0.100) 34 Example 95 444 4.72 6.98(0.134, 0.100) 51 Example 96 453 4.80 6.89 (0.134, 0.102) 58 Example 97455 4.76 6.95 (0.134, 0.102) 50 Example 98 460 4.68 6.93 (0.134, 0.100)50 Example 99 461 4.88 6.84 (0.134, 0.102) 57 Example 100 467 4.77 6.90(0.134, 0.102) 51 Example 101 470 4.98 6.05 (0.134, 0.101) 34 Example102 474 5.11 6.12 (0.134, 0.102) 48 Example 103 477 4.96 6.10 (0.134,0.100) 36 Example 104 485 5.30 6.20 (0.134, 0.101) 40 Example 105 4885.22 6.03 (0.134, 0.101) 43 Example 106 493 4.82 6.84 (0.134, 0.101) 52Example 107 511 4.84 6.97 (0.134, 0.102) 51 Example 108 516 4.90 6.81(0.134, 0.101) 56 Example 109 517 4.88 6.82 (0.134, 0.102) 57 Example110 519 4.74 6.75 (0.134, 0.101) 51 Example 111 528 4.81 6.82 (0.134,0.102) 53 Example 112 529 5.26 6.44 (0.134, 0.102) 32 Example 113 5325.21 6.38 (0.134, 0.101) 41 Example 114 535 5.44 6.47 (0.134, 0.102) 36Example 115 538 5.41 6.44 (0.134, 0.101) 43 Example 116 543 5.34 6.38(0.134, 0.101) 39 Example 117 549 5.38 6.20 (0.134, 0.103) 40 Example118 551 5.60 6.12 (0.134, 0.102) 43 Example 119 558 5.45 6.21 (0.134,0.101) 37 Example 120 560 5.44 6.22 (0.134, 0.102) 34 Example 121 5635.62 5.95 (0.134, 0.103) 42 Example 122 566 5.40 6.12 (0.134, 0.101) 39Example 123 572 5.50 5.89 (0.134, 0.100) 41 Example 124 577 5.44 6.01(0.134, 0.101) 36 Example 125 579 5.34 6.58 (0.134, 0.100) 45 Example126 584 5.38 6.93 (0.134, 0.100) 43 Example 127 585 4.91 6.32 (0.134,0.100) 41 Example 128 590 4.98 6.44 (0.134, 0.100) 40 Example 129 5945.62 6.38 (0.134, 0.100) 35 Example 130 598 4.72 6.20 (0.134, 0.102) 48Example 131 603 5.45 6.44 (0.134, 0.103) 33 Example 132 609 5.44 6.34(0.134, 0.102) 36 Example 133 611 5.62 6.20 (0.134, 0.101) 39 Example134 616 5.40 6.12 (0.134, 0.103) 44 Example 135 619 5.60 6.21 (0.134,0.102) 43 Example 136 626 5.45 6.22 (0.134, 0.101) 37 Example 137 6315.39 5.95 (0.134, 0.102) 33 Example 138 634 4.96 5.95 (0.134, 0.101) 42Example 139 638 4.91 6.13 (0.134, 0.101) 39 Example 140 639 4.91 5.85(0.134, 0.100) 41 Example 141 642 4.98 6.38 (0.134, 0.101) 42 Example142 646 5.62 6.20 (0.134, 0.100) 45 Example 143 650 4.72 6.12 (0.134,0.100) 43 Example 144 657 4.91 6.21 (0.134, 0.101) 41 Example 145 6594.98 6.22 (0.134, 0.100) 40 Example 146 663 5.62 5.95 (0.134, 0.100) 33Example 147 667 5.44 6.13 (0.134, 0.102) 36 Example 148 672 5.44 5.89(0.134, 0.102) 36 Example 149 677 5.44 6.41 (0.134, 0.102) 47 Example150 679 5.34 6.44 (0.134, 0.102) 36 Example 151 683 5.38 6.38 (0.134,0.101) 39 Example 152 688 5.38 6.20 (0.134, 0.103) 40 Example 153 6915.39 6.62 (0.134, 0.102) 43 Example 154 693 4.96 6.21 (0.134, 0.101) 37Example 155 696 4.91 6.22 (0.134, 0.102) 33 Example 156 703 4.91 6.12(0.134, 0.101) 42 Example 157 712 4.98 6.51 (0.134, 0.101) 39 Example158 713 5.62 6.21 (0.134, 0.100) 41 Example 159 716 5.39 5.95 (0.134,0.101) 34 Example 160 719 4.96 6.88 (0.134, 0.100) 45 Example 161 7234.91 6.93 (0.134, 0.102) 43 Example 162 725 4.91 6.95 (0.134, 0.100) 41Example 163 732 4.98 6.22 (0.134, 0.100) 40 Example 164 738 5.62 5.68(0.134, 0.101) 33 Example 165 743 4.96 6.88 (0.134, 0.100) 35 Example166 748 4.91 6.93 (0.134, 0.100) 43 Example 167 753 4.77 6.95 (0.134,0.100) 41 Example 168 755 4.98 6.22 (0.134, 0.100) 40 Example 169 7655.62 5.98 (0.134, 0.100) 33 Example 170 768 4.71 6.51 (0.134, 0.102) 48Example 171 779 4.72 6.53 (0.134, 0.102) 38 Example 172 784 4.91 6.78(0.134, 0.100) 43 Example 173 788 4.90 6.95 (0.134, 0.100) 41 Example174 794 4.98 6.22 (0.134, 0.100) 40 Example 175 807 5.62 5.98 (0.134,0.100) 33 Example 176 812 4.72 6.53 (0.134, 0.102) 48 Example 177 8184.74 6.59 (0.134, 0.102) 45 Example 178 827 5.42 6.13 (0.134, 0.101) 39Example 179 833 5.44 5.89 (0.134, 0.100) 41 Example 180 839 5.36 6.01(0.134, 0.101) 32 Example 181 842 4.96 6.82 (0.134, 0.100) 45 Example182 849 4.91 6.93 (0.134, 0.100) 43 Example 183 853 4.95 6.95 (0.134,0.100) 41 Example 184 857 4.98 6.22 (0.134, 0.100) 40 Example 185 8665.62 5.98 (0.134, 0.100) 33 Example 186 875 4.75 6.53 (0.134, 0.102) 40Example 187 879 4.72 6.35 (0.134, 0.102) 48 Example 188 883 4.91 6.93(0.134, 0.100) 43 Example 189 885 4.93 6.95 (0.134, 0.100) 40 Example190 893 4.98 6.21 (0.134, 0.100) 40 Example 191 895 5.62 5.98 (0.134,0.100) 34 Example 192 901 4.72 6.53 (0.134, 0.102) 35 Example 193 9044.79 6.55 (0.134, 0.102) 48 Example 194 913 5.40 6.13 (0.134, 0.101) 39Example 195 915 5.44 5.89 (0.134, 0.100) 41 Example 196 920 5.39 6.01(0.134, 0.101) 34 Comparative E1 6.00 5.12 (0.134, 0.100) 25 Example 1-1Comparative E2 6.23 4.23 (0.134, 0.111) 16 Example 1-2 Comparative E36.34 4.33 (0.134, 0.109) 14 Example 1-3 Comparative E4 6.11 4.55 (0.134,0.099) 17 Example 1-4 Comparative E5 6.08 4.64 (0.134, 0.098) 20 Example1-5

As seen from the results of Table 53, the organic electroluminescentdevice using the electron transfer layer material of the blue organicelectroluminescent device of the present disclosure had a lower drivingvoltage, and significantly improved light emission efficiency andlifetime compared to Comparative Examples 1-1, 1-2, 1-3, 1-4 and 1-5.

Such a result is considered to be due to the fact that, when using thedisclosed compound having proper length, strength and flat properties asan electron transfer layer, a compound in an excited state is made byreceiving electrons under a specific condition, and particularly when ahetero-skeleton site of the compound is formed in an excited state,excited energy moves to a stable state before the excitedhetero-skeleton site goes through other reactions, and a relativelystabilized compound is capable of efficiently transfer electrons withoutthe compound being decomposed or destroyed. For reference, those thatare stable when excited are considered to be aryl or acene compounds, orpolycyclic hetero-compounds. Accordingly, it is considered thatexcellent results in all aspects of driving, efficiency and lifetime areobtained by the compound of the present disclosure enhancing enhancedelectron-transfer properties or improved stability.

Experimental Example 2

1) Manufacture of Organic Light Emitting Device

A transparent ITO electrode thin film obtained from glass for an OLED(manufactured by Samsung-Corning Co., Ltd.) was ultrasonic cleaned usingtrichloroethylene, acetone, ethanol and distilled water consecutivelyfor 5 minutes each, stored in isopropanol, and used.

Next, an ITO substrate was installed in a substrate folder of a vacuumdepositor, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) wasintroduced to a cell in the vacuum depositor.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as below wasdeposited thereon as a light emitting layer. Specifically, in one sidecell in the vacuum depositor, H1, a blue light emitting host material,was vacuum deposited to a thickness of 200 Å, and D1, a blue lightemitting dopant material, was vacuum deposited thereon by 5% withrespect to the host material.

Subsequently, a compound of the following structural formula E1 wasdeposited to a thickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was employed to have a thicknessof 1,000 Å to manufacture an OLED. Meanwhile, all the organic compoundsrequired to manufacture the OLED were vacuum sublimation purified under10⁻⁶ torr to 10⁻⁸ torr by each material to be used in the OLEDmanufacture.

An organic electroluminescent device was manufactured in the same manneras in Experimental Example 2 except that, after forming the electrontransfer layer E1 to a thickness of 250 Å, a hole blocking layer wasformed on the electron transfer layer to a thickness of 50 Å using acompound presented in the following Table 54.

For the organic electroluminescent device manufactured as above,electroluminescent light emission (EL) properties were measured usingM7000 manufactured by McScience Inc., and with the measurement results,T₉₅ when standard luminance was 700 cd/m² was measured using a lifetimemeasurement system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the blue organicelectroluminescent device manufactured according to the presentdisclosure are as shown in Table 54.

TABLE 54 Light Driving Emission Com- Voltage Efficiency CIE Lifetimepound (V) (cd/A) (x, y) (T95) Example 197 1 4.42 6.93 (0.134, 0.099) 40Example 198 7 4.48 6.86 (0.134, 0.099) 41 Example 199 10 4.47 6.87(0.134, 0.100) 40 Example 200 17 4.67 6.64 (0.129, 0.100) 38 Example 20125 4.82 6.55 (0.130, 0.099) 36 Example 202 33 4.44 6.97 (0.134, 0.101)40 Example 203 51 4.61 6.89 (0.134, 0.103) 40 Example 204 59 5.35 6.30(0.134, 0.102) 33 Example 205 68 5.28 6.28 (0.134, 0.102) 32 Example 20683 4.57 6.74 (0.128, 0.099) 36 Example 207 98 4.62 6.72 (0.133, 0.100)37 Example 208 100 4.55 6.85 (0.134, 0.101) 39 Example 209 124 4.54 6.92(0.134, 0.101) 41 Example 210 125 4.30 6.81 (0.134, 0.101) 41 Example211 130 4.50 6.98 (0.134, 0.100) 40 Example 212 134 4.44 7.09 (0.134,0.100) 39 Example 213 149 4.64 7.08 (0.134, 0.099) 40 Example 214 1514.53 6.91 (0.134, 0.101) 41 Example 215 156 4.97 6.59 (0.134, 0.100) 34Example 216 171 5.63 6.11 (0.131, 0.098) 28 Example 217 179 5.66 6.04(0.131, 0.102) 30 Example 218 197 5.40 6.49 (0.134, 0.101) 31 Example219 203 5.60 6.22 (0.129, 0.100) 29 Example 220 219 4.70 6.01 (0.134,0.101) 36 Example 221 223 5.40 6.31 (0.134, 0.102) 31 Example 222 2364.73 6.78 (0.130, 0.100) 35 Example 223 243 4.67 6.65 (0.129, 0.098) 36Example 224 252 4.69 6.92 (0.130, 0.101) 35 Example 225 253 4.52 6.75(0.129, 0.097) 37 Example 226 265 4.80 6.89 (0.134, 0.102) 58 Example227 272 4.76 6.95 (0.134, 0.102) 50 Example 228 288 4.77 6.90 (0.134,0.102) 51 Example 229 295 5.11 6.12 (0.134, 0.102) 48 Example 230 3054.96 6.10 (0.134, 0.100) 36 Example 231 308 5.30 6.20 (0.134, 0.101) 40Example 232 319 5.22 6.03 (0.134, 0.101) 43 Example 233 334 4.90 6.81(0.134, 0.101) 56 Example 234 347 4.88 6.82 (0.134, 0.102) 57 Example235 352 4.74 6.75 (0.134, 0.101) 51 Example 236 358 4.81 6.82 (0.134,0.102) 53 Example 237 379 5.16 6.20 (0.134, 0.101) 38 Example 238 3825.15 6.42 (0.134, 0.102) 39 Example 239 389 5.31 6.30 (0.134, 0.103) 37Example 240 406 4.82 6.35 (0.134, 0.100) 50 Example 241 415 4.84 6.60(0.134, 0.100) 49 Example 242 425 4.91 6.69 (0.134, 0.102) 51 Example243 433 4.90 6.71 (0.134, 0.102) 50 Example 244 444 4.72 6.98 (0.134,0.100) 51 Example 245 453 4.80 6.89 (0.134, 0.102) 58 Example 246 4554.76 6.95 (0.134, 0.102) 50 Example 247 467 4.77 6.90 (0.134, 0.102) 51Example 248 470 4.98 6.05 (0.134, 0.101) 34 Example 249 488 5.22 6.03(0.134, 0.101) 43 Example 250 493 4.82 6.84 (0.134, 0.101) 52 Example251 511 4.84 6.97 (0.134, 0.102) 51 Example 252 519 4.74 6.75 (0.134,0.101) 51 Example 253 528 4.81 6.82 (0.134, 0.102) 53 Example 254 5295.26 6.44 (0.134, 0.102) 32 Example 255 532 5.21 6.38 (0.134, 0.101) 41Example 256 535 5.44 6.47 (0.134, 0.102) 36 Example 257 549 5.38 6.20(0.134, 0.103) 40 Example 258 551 5.60 6.12 (0.134, 0.102) 43 Example259 558 5.45 6.21 (0.134, 0.101) 37 Example 260 560 5.44 6.22 (0.134,0.102) 34 Example 261 572 5.50 5.89 (0.134, 0.100) 41 Example 262 5775.44 6.01 (0.134, 0.101) 36 Example 263 585 4.91 6.32 (0.134, 0.100) 41Example 264 590 4.98 6.44 (0.134, 0.100) 40 Example 265 594 5.62 6.38(0.134, 0.100) 35 Example 266 609 5.44 6.34 (0.134, 0.102) 36 Example267 611 5.62 6.20 (0.134, 0.101) 39 Example 268 619 5.60 6.21 (0.134,0.102) 43 Example 269 626 5.45 6.22 (0.134, 0.101) 37 Example 270 6344.96 5.95 (0.134, 0.101) 42 Example 271 646 5.62 6.20 (0.134, 0.100) 45Example 272 650 4.72 6.12 (0.134, 0.100) 43 Example 273 677 5.44 6.41(0.134, 0.102) 47 Example 274 688 5.38 6.20 (0.134, 0.103) 40 Example275 691 5.39 6.62 (0.134, 0.102) 43 Example 276 703 4.91 6.12 (0.134,0.101) 42 Example 277 712 4.98 6.51 (0.134, 0.101) 39 Example 278 7194.96 6.88 (0.134, 0.100) 45 Example 279 723 4.91 6.93 (0.134, 0.102) 43Example 280 755 4.98 6.22 (0.134, 0.100) 40 Example 281 765 5.62 5.98(0.134, 0.100) 33 Example 282 779 4.72 6.53 (0.134, 0.102) 38 Example283 784 4.91 6.78 (0.134, 0.100) 43 Example 284 794 4.98 6.22 (0.134,0.100) 40 Example 285 807 5.62 5.98 (0.134, 0.100) 33 Example 286 8124.72 6.53 (0.134, 0.102) 48 Example 287 827 5.42 6.13 (0.134, 0.101) 39Example 288 833 5.44 5.89 (0.134, 0.100) 41 Example 289 842 4.96 6.82(0.134, 0.100) 45 Example 290 857 4.98 6.22 (0.134, 0.100) 40 Example291 866 5.62 5.98 (0.134, 0.100) 33 Example 292 879 4.72 6.35 (0.134,0.102) 48 Example 293 883 4.91 6.93 (0.134, 0.100) 43 Example 294 8955.62 5.98 (0.134, 0.100) 34 Example 295 901 4.72 6.53 (0.134, 0.102) 35Example 296 904 4.79 6.55 (0.134, 0.102) 48 Example 297 920 5.39 6.01(0.134, 0.101) 34 Comparative E1 6.02 5.01 (0.134, 0.100) 21 Example 2-1Comparative E2 6.55 4.44 (0.134, 0.102) 11 Example 2-2 Comparative E36.54 4.46 (0.134, 0.099) 10 Example 2-3 Comparative E4 6.23 4.65 (0.134,0.101) 19 Example 2-4 Comparative E5 6.29 4.67 (0.134, 0.101) 18 Example2-5

As seen from the results of Table 54, the organic light emitting deviceusing the hole blocking layer material of the blue organic lightemitting device of the present disclosure had a lower driving voltage,and significantly improved light emission efficiency and lifetimecompared to Comparative Examples 2-1, 2-2, 2-3, 2-4 and 2-5.

Such a reason is due to the fact that the heterocyclic compound ofChemical Formula 1 of the present application is a bipolar type havingboth a P-type and an N-type, and is capable of blocking hole leakage andeffectively trapping excitons in the light emitting layer.

Experimental Example 3

1) Manufacture of Organic Light Emitting Device

A glass substrate on which ITO was coated as a thin film to a thicknessof 1500 Å was cleaned with distilled water ultrasonic waves. After thecleaning with distilled water was finished, the substrate was ultrasoniccleaned with solvents such as acetone, methanol and isopropyl alcohol,then dried, and UVO treatment was carried out for 5 minutes in a UVcleaner using UV. After that, the substrate was transferred to a plasmacleaner (PT), and plasma treatment was carried out under vacuum for ITOwork function and remaining film removal, and the substrate wastransferred to a thermal deposition apparatus for organic deposition.

On the transparent ITO electrode (anode), an organic material was formedin a 2 stack white organic light emitting device (WOLED) structure. Asfor the first stack, TAPC was thermal vacuum deposited to a thickness of300 Å first to form a hole transfer layer. After forming the holetransfer layer, a light emitting layer was thermal vacuum depositedthereon as follows. The light emitting layer was deposited to 300 Å bydoping Flrpic to TCzl, a host, by 8% as a blue phosphorescent dopant.After forming an electron transfer layer to 400 Å using TmPyPB, a chargegeneration layer was formed to 100 Å by doping Cs₂CO₃ to the compounddescribed in the following Table 55 by 20%.

As for the second stack, MoO₃ was thermal vacuum deposited to athickness of 50 Å first to form a hole injection layer. A hole transferlayer, a common layer, was formed by doping MoO₃ to TAPC by 20% to 100 Åand depositing TAPC to 300 Å. A light emitting layer was depositedthereon to 300 Å by doping Ir(ppy)₃, a green phosphorescent dopant, toTCzl, a host, by 8%, and an electron transfer layer was formed to 600 Åusing TmPyPB. Lastly, an electron injection layer was formed on theelectron transfer layer by depositing lithium fluoride (LiF) to athickness of 10 Å, and then a cathode was formed on the electroninjection layer by depositing an aluminum (Al) cathode to a thickness of1,200 Å to manufacture an organic electroluminescent device.

Meanwhile, all the organic compounds required to manufacture the OLEDwere vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr by eachmaterial to be used in the OLED manufacture.

For the organic electroluminescent devices manufactured as above,electroluminescent light emission (EL) properties were measured usingM7000 manufactured by McScience Inc., and with the measurement results,195 when standard luminance was 3,500 cd/m² was measured using alifetime measurement system (M6000) manufactured by McScience Inc.Results of measuring a driving voltage, light emission efficiency,external quantum efficiency and a color coordinate (CIE) of the whiteorganic electroluminescent device manufactured according to the presentdisclosure are as shown in Table 55.

TABLE 55 Light Driving Emission Com- Voltage Efficiency CIE Lifetimepound (V) (cd/A) (x, y) (T95) Example 298 921 7.29 65.55 (0.220, 0.432)53 Example 299 924 7.31 66.32 (0.221, 0.433) 51 Example 300 925 7.0567.93 (0.221, 0.428) 50 Example 301 926 7.06 69.82 (0.221, 0.440) 42Example 302 928 7.08 69.45 (0.220, 0.430) 40 Example 303 929 7.12 68.55(0.215, 0.422) 44 Example 304 931 7.08 68.21 (0.214, 0.422) 45 Example305 935 7.02 67.44 (0.212, 0.417) 40 Example 306 937 7.09 68.01 (0.211,0.422) 42 Example 307 938 7.11 69.44 (0.223, 0.428) 41 Example 308 9397.02 68.08 (0.222, 0.430) 42 Example 309 940 7.04 69.11 (0.231, 0.434)40 Example 310 942 7.08 69.45 (0.220, 0.430) 40 Example 311 944 7.1268.55 (0.216, 0.426) 35 Comparative E2 8.57 33.11 (0.201, 0.398) 9Example 3-1 Comparative E3 8.43 32.12 (0.189, 0.388) 6 Example 3-2Comparative E4 8.46 33.01 (0.188, 0.388) 6 Example 3-3 Comparative E58.52 32.56 (0.199, 0.398) 8 Example 3-4

As seen from the results of Table 55, the organic electroluminescentdevice using the charge generation layer material of the 2-stack whiteorganic electroluminescent device of the present disclosure had a lowerdriving voltage and improved light emission efficiency compared toComparative Examples 3-1, 3-2, 3-3 and 3-4.

Such a result is considered to be due to the fact that the compound ofthe present disclosure used as the N-type charge generation layer formedwith the disclosed skeleton having proper length, strength and flatproperties and a proper hetero-compound capable of binding with a metalforms a gap state in the N-type charge generation layer by doping analkali metal or an alkaline earth metal, and electrons produced from theP-type charge generation layer are readily injected to the electrontransfer layer through the gap state produced in the N-type chargegeneration layer. Accordingly, it is considered that the P-type chargegeneration layer favorably injects and transfers electrons to the N-typecharge generation layer, and as a result, a driving voltage was lowered,and efficiency and lifetime were improved in the organic light emittingdevice.

1. A heterocyclic compound represented by the following Chemical Formula1:

wherein, in Chemical Formula 1, X is O or S; L1 and L2 are the same asor different from each other, and each independently a substituted orunsubstituted arylene group; or a substituted or unsubstitutedheteroarylene group; Z1 and Z2 are the same as or different from eachother, and each independently hydrogen; a substituted or unsubstitutedalkyl group; a substituted or unsubstituted aryl group; a substituted orunsubstituted heteroaryl group; —SiRR′R″; or —P(═O)RR′; R_(a) and R_(b)are the same as or different from each other, and each independentlyhydrogen; deuterium; a halogen group; —CN; a substituted orunsubstituted alkyl group; a substituted or unsubstituted alkenyl group;a substituted or unsubstituted alkynyl group; a substituted orunsubstituted alkoxy group; a substituted or unsubstituted cycloalkylgroup; a substituted or unsubstituted heterocycloalkyl group; asubstituted or unsubstituted aryl group; a substituted or unsubstitutedheteroaryl group; —SiRR′R″; —P(═O)RR′; and an amine group unsubstitutedor substituted with a substituted or unsubstituted alkyl group, asubstituted or unsubstituted aryl group, or a substituted orunsubstituted heteroaryl group, or two or more groups adjacent to eachother bond to each other to form a substituted or unsubstitutedaliphatic or aromatic hydrocarbon ring; R, R′ and R″ are the same as ordifferent from each other, and each independently hydrogen; deuterium;—CN; a substituted or unsubstituted alkyl group; a substituted orunsubstituted cycloalkyl group; a substituted or unsubstituted arylgroup; or a substituted or unsubstituted heteroaryl group; p and n arean integer of 1 to 3; m, q and s are an integer of 1 to 4; r is aninteger of 0 to 4; and when r is an integer of 0 and Z2 is hydrogen, nis an integer of 2 or 3, and R_(b) is a substituted or unsubstitutedaryl group; or a substituted or unsubstituted heteroaryl group, or twoor more groups adjacent to each other bond to each other to form asubstituted or unsubstituted aliphatic or aromatic hydrocarbon ring. 2.The heterocyclic compound of claim 1, wherein the “substituted orunsubstituted” means being substituted with one or more substituentsselected from the group consisting of C1 to C60 linear or branchedalkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear orbranched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 toC60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic orpolycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl;—SiRR′R″; —P(═O)RR′; C1 to C20 alkylamine; C6 to C60 monocyclic orpolycyclic arylamine; and C2 to C60 monocyclic or polycyclicheteroarylamine, or being unsubstituted, or being substituted with asubstituent linking two or more substituents selected from among thesubstituents illustrated above, or being unsubstituted; and R, R′ and R″have the same definitions as in Chemical Formula
 1. 3. The heterocycliccompound of claim 1, wherein Chemical Formula 1 is represented by anyone of the following Chemical Formulae 2 to 5:

in Chemical Formulae 2 to 5, L1, L2, Z1, Z2, X, p, q, r and s each havethe same definition as in Chemical Formula
 1. 4. The heterocycliccompound of claim 1, wherein R_(a) is hydrogen.
 5. The heterocycliccompound of claim 1, wherein L1 is a substituted or unsubstitutedmonocyclic or polycyclic C6 to C40 arylene group; or a substituted orunsubstituted C2 to C40 N-containing heteroarylene group; Z1 ishydrogen; a C6 to C40 aryl group unsubstituted or substituted with oneor more substituents selected from the group consisting of a C6 to C40aryl group and a C2 to C40 heteroaryl group; a C2 to C40 heteroarylgroup; or —P(═O)RR′; and R and R′ have the same definitions as inChemical Formula
 1. 6. The heterocyclic compound of claim 1, wherein L2is a C6 to C40 arylene group; or a C2 to C40 heteroarylene group; Z2 ishydrogen; a C6 to C40 aryl group unsubstituted or substituted with a C6to C40 heteroaryl group; a C2 to C40 heteroaryl group; or P(═O)RR′; andR and R′ are the same as or different from each other, and eachindependently hydrogen; a substituted or unsubstituted aryl group; or asubstituted or unsubstituted heteroaryl group.
 7. The heterocycliccompound of claim 1, wherein Chemical Formula 1 is represented by anyone of the following Chemical Formulae 6 to 11:

in Chemical Formulae 6 to 11, R_(a), L1, Z1, p, q and m each have thesame definition as in Chemical Formula
 1. 8. The heterocyclic compoundof claim 1, wherein Chemical Formula 1 is represented by any one of thefollowing compounds:


9. An organic light emitting device comprising: a first electrode; asecond electrode provided opposite to the first electrode; and one ormore organic material layers provided between the first electrode andthe second electrode, wherein one or more layers of the organic materiallayers comprise the heterocyclic compound of claim
 1. 10. The organiclight emitting device of claim 9, wherein the organic material layercomprises a light emitting layer, and the light emitting layer comprisesthe heterocyclic compound.
 11. The organic light emitting device ofclaim 9, wherein the organic material layer comprises a light emittinglayer, the light emitting layer comprises a host material, and the hostmaterial comprises the heterocyclic compound.
 12. The organic lightemitting device of claim 9, wherein the organic material layer comprisesan electron injection layer or an electron transfer layer, and theelectron injection layer or the electron transfer layer comprises theheterocyclic compound.
 13. The organic light emitting device of claim 9,wherein the organic material layer comprises an electron blocking layeror a hole blocking layer, and the electron blocking layer or the holeblocking layer comprises the heterocyclic compound.
 14. The organiclight emitting device of claim 9, further comprising one, two or morelayers selected from the group consisting of a light emitting layer, ahole injection layer, a hole transfer layer. an electron injectionlayer, an electron transfer layer, an electron blocking layer and a holeblocking layer.
 15. The organic light emitting device of claim 9,comprising: a first electrode; a first stack provided on the firstelectrode and comprising a first light emitting layer; a chargegeneration layer provided on the first stack; a second stack provided onthe charge generation layer and comprising a second light emittinglayer; and a second electrode provided on the second stack.
 16. Theorganic light emitting device of claim 15, wherein the charge generationlayer comprises the heterocyclic compound.